Compound, material for organic electroluminescent elements, organic electroluminescent element, and electronic device

ABSTRACT

A compound represented by the following formula (1) wherein the symbols are as defined in the description, and an organic electroluminescent device containing the compound.

This application is a continuation application of U.S. application Ser.No. 17/704,646 filed Mar. 25, 2022, allowed, which is a continuationapplication of PCT/JP2021/013412 filed Mar. 29, 2021 and claims thebenefit of JP 2020-217191 filed Dec. 25, 2020 and JP 2020-064541 filedMar. 31, 2020.

TECHNICAL FIELD

The present disclosure relates to a compound, a material for organicelectroluminescent devices, an organic electroluminescent device, and anelectronic device including the organic luminescent device.

BACKGROUND ART

In general, an organic electroluminescent device (which may behereinafter referred to as an “organic EL device”) is constituted by ananode, a cathode, and an organic layer intervening between the anode andthe cathode. In application of a voltage between both the electrodes,electrons from the cathode side and holes from the anode side areinjected into a light emitting region, and the injected electrons andholes are recombined in the light emitting region to generate an excitedstate, which then returns to the ground state to emit light.Accordingly, development of a material that efficiently transportselectrons or holes into the light emitting region, and promotesrecombination of the electrons and holes is important for providing ahigh-performance organic EL device.

PTLs 1 to 13 describe compounds used for a material for organicelectroluminescent devices.

CITATION LIST Patent Literature

-   PTL 1: KR2018-0082124A-   PTL 2: US2015/0236267A1-   PTL 3: WO2009/145016A1-   PTL 4: CN109485577A-   PTL 5: KR2019-0003329A-   PTL 6: KR2017-0088313A-   PTL 7: WO2019/206292A1-   PTL 8: WO2019/185060A1-   PTL 9: US2019/0140177A1-   PTL 10: WO2019/168367A1-   PTL 11: US2019/0165273A1-   PTL 12: WO2012/079678A1-   PTL 13: WO2020004235A1

SUMMARY Technical Problem

Various compounds for organic EL devices have been reported, but acompound that further enhances the capability of an organic EL devicehas been still demanded.

The present disclosure has been made for solving the problem, and anobject thereof is to provide a compound that further improves thecapability of an organic EL device, an organic EL device having afurther improved device capability, and an electronic device includingthe organic EL device.

Solution to Problem

As a result of the continued investigations by the present inventors onthe capabilities of organic EL devices containing the compoundsdescribed in the above-mentioned patent publications and anothercompounds, it has been found that a monoamine represented by thefollowing formula (1) can provide an organic EL device having a furtherimproved capability.

In one embodiment, the present disclosure relates to the following [1]to [25].

[1] A compound represented by the following formula (1):

wherein

Ar¹ and Ar² each independently represent a group represented by any ofthe following formulae (10) to (14):

wherein

R¹¹ to R¹⁵, R²¹ to R²⁶, R⁴¹ to R⁴⁸, R⁵¹ to R⁶² and R⁷¹ to R⁷⁸ eachindependently represent a hydrogen atom, a substituted or unsubstitutedalkyl group having 1 to 50 carbon atoms, a substituted or unsubstitutedcycloalkyl group having 3 to 50 ring carbon atoms, a halogen atom, acyano group, a nitro group, a substituted or unsubstituted aryl grouphaving 6 to 50 ring carbon atoms, or a substituted or unsubstitutedheterocyclic group having 5 to 50 ring atoms,

R³¹ to R³⁵ each independently represent a hydrogen atom, a substitutedor unsubstituted alkyl group having 1 to 50 carbon atoms, unsubstitutedcycloalkyl group having 3 to 6 ring carbon atoms, a halogen atom, acyano group, a nitro group, an unsubstituted aryl group having 6 to 50ring carbon atoms, or a substituted or unsubstituted heterocyclic grouphaving 5 to 50 ring atoms,

X represents an oxygen atom, a sulfur atom, or NR⁸¹,

R⁸¹ represents a hydrogen atom, a substituted or unsubstituted alkylgroup having 1 to 50 carbon atoms, a substituted or unsubstituted arylgroup having 6 to 50 ring carbon atoms, or a substituted orunsubstituted heterocyclic group having 5 to 50 ring atoms,

provided that,

one selected from R¹¹ to R¹⁵ is a single bond bonding to *c,

one selected from R²¹ to R²⁶ is a single bond bonding to *d, the otherone selected from R²¹ to R²⁶ is a single bond bonding to *e,

one selected from R⁴⁵ to R⁴⁸ is a single bond bonding to *f,

one selected from R⁵⁹ to R⁶² is a single bond bonding to *g,

one selected from R⁷⁵ to R⁷⁸ and R⁸¹ is a single bond bonding to *i,

*h bonds to one selected from the carbon atoms *4 to *8,

** represents a bonding position to the central nitrogen atom,

m is 0 or 1, n is 0 or 1,

in the formulae (10) to (12) and the formula (14), when m is 0 and n is0, *e bonds to the central nitrogen atom, when m is 0 and n is 1, *cbonds to the central nitrogen atom, and when m is 1 and n is 0, *e bondsto one selected from R¹¹ to R¹⁵,

in the formula (13), when m is 0 and n is 1, *c bonds to the centralnitrogen atom, when m is 1 and n is 0, *e bonds to one selected from R¹¹to R¹⁵, a case where m is 0 and n is 0 is excluded,

in the formula (14), when m is 0 and n is 1, and when m is 1 and n is 0,one selected from R⁷⁵ to R⁷⁸ is a single bond bonding to *i,

adjacent two selected from R¹¹ to R¹⁵ that are not a single bond,adjacent two selected from R²¹ to R²⁶ and adjacent two selected from R³¹to R³⁵ that are not a single bond, adjacent two selected from R⁴¹ to R⁴⁸that are not a single bond, adjacent two selected from R⁵¹ to R⁶² thatare not a single bond, and adjacent two selected from R⁷¹ to R⁷⁸ thatare not a single bond do not bond to each other and therefore do notform a cyclic structure,

the benzene ring A and the benzene ring B, the benzene ring A and thebenzene ring C, the benzene ring B and the benzene ring C, the benzenering A and the naphthalene ring, and the benzene ring B and thenaphthalene ring do not crosslink,

*a bonds to one selected from the carbon atoms *1 to *3,

R¹ to R⁴ each independently represent a hydrogen atom, or a substitutedor unsubstituted alkyl group having 1 to 50 carbon atoms,

provided that,

one selected from R¹ to R⁴ is a single bond bonding to *b,

adjacent two selected from R¹ to R⁴ that are not a single bond bondingto *b do not bond to each other and therefore do not form a cyclicstructure,

R⁵ to R⁹ each independently represent a hydrogen atom, a substituted orunsubstituted alkyl group having 1 to 50 carbon atoms, or a substitutedor unsubstituted phenyl group,

provided that,

adjacent two selected from R⁵ to R⁹ each independently may bond to eachother to form a substituted or unsubstituted cyclic structure, or maynot bond to each other and therefore may not form a cyclic structure.

[2] The compound of [1], wherein Ar¹ and Ar² each are independently agroup represented by any of the formulae (20) to (24):

wherein

R¹¹ to R¹⁵, R²¹, R²², R²⁴, R²⁵, R³¹ to R³⁵, R⁴¹ to R⁴⁸, R⁵¹ to R⁶², R⁷¹to R⁷⁸, *f, *g, *h, *i, X, **, m, n, the benzene ring A, the benzenering B and the benzene ring C are as defined in the formula (1).

[3] The compound of [1] or [2], wherein

R⁴⁵ or R⁴⁶ is a single bond bonding to *f,

R⁶⁰ or R⁶¹ is a single bond bonding to *g, and

*h bonds to the carbon atom *8.

[4] The compound of any one of [1] to [3], wherein in the formulae (10)to (12) and the formula (14). m is 0 and n is 0.[5] The compound of any one of [1] to [3], wherein m is 1 and n is 1.[6] The compound of any one of [1] to [3], wherein m is 0 and n is 1.[7] The compound of any one of [1] to [6], wherein Ar¹ and Ar² each areindependently a group represented by any of the formulae (10), (11) and(14).[8] The compound of any one of [1] to [7], wherein at least one of Ar¹and Ar² is a group represented by the formula (11).[9] The compound of any one of [1] to [8], wherein X is an oxygen atom.[10] The compound of any one of [1] to [9], wherein R⁴⁵ is a single bondbonding to *f.[11] The compound of any one of [1] to [10], wherein R⁷⁵ is a singlebond bonding to *i.[12] The compound of any one of [1] to [11], wherein *a bonds to thecarbon atom *3.[13] The compound of any one of [1] to [12], wherein R² or R³ is asingle bond bonding to *b.[14] The compound of any one of [1] to [13], wherein R¹ to R⁴ that arenot a single bond bonding to *b are all hydrogen atoms.[15] The compound of any one of [1] to [14], wherein R⁵ to R⁹ are allhydrogen atoms.[16] The compound of any one of [1] to [15], wherein the compoundcontains at least one deuterium.[17] A material for an organic electroluminescent device containing thecompound of any one of [1] to [16].[18] An organic electroluminescent device comprising an anode, acathode, and organic layers intervening between the anode and thecathode, the organic layers including a light emitting layer, at leastone layer of the organic layers containing the compound of any one of[1] to [16].[19] The organic electroluminescent device of [18], wherein the organiclayer includes a hole transporting zone between the anode and the lightemitting layer, and the hole transporting zone contains the compound.[20] The organic electroluminescent device of [19], wherein the holetransporting zone includes a first hole transporting layer on the anodeside and a second hole transporting layer on the cathode side, and thefirst hole transporting layer or the second hole transporting layer orboth the two contain the compound.[21] The organic electroluminescent device of [20], wherein the secondhole transporting layer contains the compound.[22] The organic electroluminescent device of [20] or [21], wherein thesecond hole transporting layer is adjacent to the light emitting layer.[23] The organic electroluminescent device of any one of [18] to [22],wherein the light emitting layer contains a fluorescent dopant.[24] The organic electroluminescent device of any one of [18] to [22],wherein the light emitting layer contains a phosphorescent dopant.[25] An electronic device comprising the organic electroluminescentdevice of any one of [18] to [24].

In one embodiment, the present disclosure provides a compoundrepresented by the following formula (1):

wherein

In another embodiment, Ar¹ is a group represented by the formula (10) or(11), and Ar² is a group represented by any of the formulae (10) to(14):

wherein

R¹¹ to R¹⁵, R²¹ to R²⁶, R⁴¹ to R⁴⁸, R⁵¹ to R⁶² and R⁷¹ to R⁷⁸ eachindependently represent a hydrogen atom, a substituted or unsubstitutedalkyl group having 1 to 50 carbon atoms, a substituted or unsubstitutedcycloalkyl group having 3 to 50 ring carbon atoms, a halogen atom, acyano group, a nitro group, a substituted or unsubstituted aryl grouphaving 6 to 50 ring carbon atoms, or a substituted or unsubstitutedheterocyclic group having 5 to 50 ring atoms,

R³¹ to R³⁵ each independently represent a hydrogen atom, a substitutedor unsubstituted alkyl group having 1 to 50 carbon atoms, unsubstitutedcycloalkyl group having 3 to 6 ring carbon atoms, a halogen atom, acyano group, a nitro group, an unsubstituted aryl group having 6 to 50ring carbon atoms, or a substituted or unsubstituted heterocyclic grouphaving 5 to 50 ring atoms,

X represents an oxygen atom, a sulfur atom, or NR⁸¹,

R⁸¹ represents a hydrogen atom, a substituted or unsubstituted alkylgroup having 1 to 50 carbon atoms, a substituted or unsubstituted arylgroup having 6 to 50 ring carbon atoms, or a substituted orunsubstituted heterocyclic group having 5 to 50 ring atoms,

provided that,

one selected from R¹¹ to R¹⁵ is a single bond bonding to *c,

one selected from R²¹ to R²⁶ is a single bond bonding to *d, the otherone selected from R²¹ to R²⁶ is a single bond bonding to *e,

one selected from R⁴⁵ to R⁴⁸ is a single bond bonding to *f,

one selected from R⁵⁹ to R⁶² is a single bond bonding to *g,

one selected from R⁷⁵ to R⁷⁸ and R⁸¹ is a single bond bonding to *i,

*h bonds to one selected from the carbon atoms *4 to *8,

** represents a bonding position to the central nitrogen atom,

m is 0 or 1, n is 0 or 1,

in the formulae (10) to (12) and the formula (14), when m is 0 and n is0, *e bonds to the central nitrogen atom, when m is 0 and n is 1, *cbonds to the central nitrogen atom, and when m is 1 and n is 0, *e bondsto one selected from R¹¹ to R¹⁵,

in the formula (13), when m is 0 and n is 1, *c bonds to the centralnitrogen atom, when m is 1 and n is 0, *e bonds to one selected from R¹¹to R¹⁵, a case where m is 0 and n is 0 is excluded,

in the formula (14), when m is 0 and n is 1, and when m is 1 and n is 0,one selected from R⁷⁵ to R⁷⁸ is a single bond bonding to *i,

adjacent two selected from R¹¹ to R¹⁵ that are not a single bond,adjacent two selected from R²¹ to R²⁶ and adjacent two selected from R³¹to R³⁵ that are not a single bond, adjacent two selected from R⁴¹ to R⁴⁸that are not a single bond, adjacent two selected from R⁵¹ to R⁶² thatare not a single bond, and adjacent two selected from R⁷¹ to R⁷⁸ thatare not a single bond do not bond to each other and therefore do notform a cyclic structure,

the benzene ring A and the benzene ring B, the benzene ring A and thebenzene ring C, the benzene ring B and the benzene ring C, the benzenering A and the naphthalene ring, and the benzene ring B and thenaphthalene ring do not crosslink,

*a bonds to one selected from the carbon atoms *1 to *3,

R¹ to R⁴ each independently represent a hydrogen atom, or a substitutedor unsubstituted alkyl group having 1 to 50 carbon atoms,

provided that,

one selected from R¹ to R⁴ is a single bond bonding to *b,

adjacent two selected from R¹ to R⁴ that are not a single bond bondingto *b do not bond to each other and therefore do not form a cyclicstructure,

R⁵ to R⁹ each independently represent a hydrogen atom, a substituted orunsubstituted alkyl group having 1 to 50 carbon atoms, or a substitutedor unsubstituted phenyl group,

provided that,

adjacent two selected from R⁵ to R⁹ each independently may bond to eachother to form a substituted or unsubstituted cyclic structure, or maynot bond to each other and therefore may not form a cyclic structure.

In still another embodiment, the present disclosure provides a materialfor an organic EL device containing the compound represented by theformula (1).

In still another embodiment, the present disclosure provides an organicelectroluminescent device including an anode, a cathode, and organiclayers intervening between the anode and the cathode, the organic layersincluding a light emitting layer, at least one layer of the organiclayers containing the compound represented by the formula (1).

In a further embodiment, the present disclosure provides an electronicdevice including the organic electroluminescent device.

Advantageous Effects of Invention

An organic EL device containing the compound represented by the formula(1) shows an improved device capability.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 is a schematic illustration showing an example of the layerconfiguration of the organic EL device according to one embodiment ofthe present disclosure.

FIG. 2 is a schematic illustration showing another example of the layerconfiguration of the organic EL device according to one embodiment ofthe present disclosure.

DETAILED DESCRIPTION OF EMBODIMENTS Definitions

In the description herein, the hydrogen atom encompasses isotopesthereof having different numbers of neutrons, i.e., a light hydrogenatom (protium), a heavy hydrogen atom (deuterium), and tritium.

In the description herein, the bonding site where the symbol, such as“R”, or “D” representing a deuterium atom is not shown is assumed tohave a hydrogen atom, i.e., a protium atom, a deuterium atom, or atritium atom, bonded thereto.

In the description herein, the number of ring carbon atoms shows thenumber of carbon atoms among the atoms constituting the ring itself of acompound having a structure including atoms bonded to form a ring (suchas a monocyclic compound, a condensed ring compound, a bridged compound,a carbocyclic compound, and a heterocyclic compound). In the case wherethe ring is substituted by a substituent, the carbon atom contained inthe substituent is not included in the number of ring carbon atoms. Thesame definition is applied to the “number of ring carbon atoms”described hereinafter unless otherwise indicated. For example, a benzenering has 6 ring carbon atoms, a naphthalene ring has 10 ring carbonatoms, a pyridine ring has 5 ring carbon atoms, and a furan ring has 4ring carbon atoms. For example, 9,9-diphenylfluorenyl group has 13 ringcarbon atoms, and 9,9′-spirobifluorenyl group has 25 ring carbon atoms.

In the case where a benzene ring has, for example, an alkyl groupsubstituted thereon as a substituent, the number of carbon atoms of thealkyl group is not included in the number of ring carbon atoms of thebenzene ring. Accordingly, a benzene ring having an alkyl groupsubstituted thereon has 6 ring carbon atoms. In the case where anaphthalene ring has, for example, an alkyl group substituted thereon asa substituent, the number of carbon atoms of the alkyl group is notincluded in the number of ring carbon atoms of the naphthalene ring.Accordingly, a naphthalene ring having an alkyl group substitutedthereon has 10 ring carbon atoms.

In the description herein, the number of ring atoms shows the number ofatoms constituting the ring itself of a compound having a structureincluding atoms bonded to form a ring (such as a monocyclic ring, acondensed ring, and a set of rings) (such as a monocyclic compound, acondensed ring compound, a bridged compound, a carbocyclic compound, anda heterocyclic compound). The atom that does not constitute the ring(such as a hydrogen atom terminating the bond of the atom constitutingthe ring) and, in the case where the ring is substituted by asubstituent, the atom contained in the substituent are not included inthe number of ring atoms. The same definition is applied to the “numberof ring atoms” described hereinafter unless otherwise indicated. Forexample, a pyridine ring has 6 ring atoms, a quinazoline ring has 10ring atoms, and a furan ring has 5 ring atoms. For example, the numberof hydrogen atoms bonded to a pyridine ring or atoms constituting asubstituent is not included in the number of ring atoms of the pyridinering. Accordingly, a pyridine ring having a hydrogen atom or asubstituent bonded thereto has 6 ring atoms. For example, the number ofhydrogen atoms bonded to carbon atoms of a quinazoline ring or atomsconstituting a substituent is not included in the number of ring atomsof the quinazoline ring. Accordingly, a quinazoline ring having ahydrogen atom or a substituent bonded thereto has 10 ring atoms.

In the description herein, the expression “having XX to YY carbon atoms”in the expression “substituted or unsubstituted ZZ group having XX to YYcarbon atoms” means the number of carbon atoms of the unsubstituted ZZgroup, and, in the case where the ZZ group is substituted, the number ofcarbon atoms of the substituent is not included. Herein, “YY” is largerthan “XX”, “XX” represents an integer of 1 or more, and “YY” representsan integer of 2 or more.

In the description herein, the expression “having XX to YY atoms” in theexpression “substituted or unsubstituted ZZ group having XX to YY atoms”means the number of atoms of the unsubstituted ZZ group, and, in thecase where the ZZ group is substituted, the number of atoms of thesubstituent is not included. Herein, “YY” is larger than “XX”, “XX”represents an integer of 1 or more, and “YY” represents an integer of 2or more.

In the description herein, an unsubstituted ZZ group means the casewhere the “substituted or unsubstituted ZZ group” is an “unsubstitutedZZ group”, and a substituted ZZ group means the case where the“substituted or unsubstituted ZZ group” is a “substituted ZZ group”.

In the description herein, the expression “unsubstituted” in theexpression “substituted or unsubstituted ZZ group” means that hydrogenatoms in the ZZ group are not substituted by a substituent. The hydrogenatoms in the “unsubstituted ZZ group” each are a protium atom, adeuterium atom, or a tritium atom.

In the description herein, the expression “substituted” in theexpression “substituted or unsubstituted ZZ group” means that one ormore hydrogen atom in the ZZ group is substituted by a substituent. Theexpression “substituted” in the expression “BB group substituted by anAA group” similarly means that one or more hydrogen atom in the BB groupis substituted by the AA group.

Substituents in Description

The substituents described in the description herein will be explained.

In the description herein, the number of ring carbon atoms of the“unsubstituted aryl group” is 6 to 50, preferably 6 to 30, and morepreferably 6 to 18, unless otherwise indicated in the description.

In the description herein, the number of ring atoms of the“unsubstituted heterocyclic group” is 5 to 50, preferably 5 to 30, andmore preferably 5 to 18, unless otherwise indicated in the description.

In the description herein, the number of carbon atoms of the“unsubstituted alkyl group” is 1 to 50, preferably 1 to 20, and morepreferably 1 to 6, unless otherwise indicated in the description.

In the description herein, the number of carbon atoms of the“unsubstituted alkenyl group” is 2 to 50, preferably 2 to 20, and morepreferably 2 to 6, unless otherwise indicated in the description.

In the description herein, the number of carbon atoms of the“unsubstituted alkynyl group” is 2 to 50, preferably 2 to 20, and morepreferably 2 to 6, unless otherwise indicated in the description.

In the description herein, the number of ring carbon atoms of the“unsubstituted cycloalkyl group” is 3 to 50, preferably 3 to 20, andmore preferably 3 to 6, unless otherwise indicated in the description.

In the description herein, the number of ring carbon atoms of the“unsubstituted arylene group” is 6 to 50, preferably 6 to 30, and morepreferably 6 to 18, unless otherwise indicated in the description.

In the description herein, the number of ring atoms of the“unsubstituted divalent heterocyclic group” is 5 to 50, preferably 5 to30, and more preferably 5 to 18, unless otherwise indicated in thedescription.

In the description herein, the number of carbon atoms of the“unsubstituted alkylene group” is 1 to 50, preferably 1 to 20, and morepreferably 1 to 6, unless otherwise indicated in the description.

Substituted or Unsubstituted Aryl Group

In the description herein, specific examples (set of specific examplesG1) of the “substituted or unsubstituted aryl group” include theunsubstituted aryl groups (set of specific examples G1A) and thesubstituted aryl groups (set of specific examples G1B) shown below.(Herein, the unsubstituted aryl group means the case where the“substituted or unsubstituted aryl group” is an “unsubstituted arylgroup”, and the substituted aryl group means the case where the“substituted or unsubstituted aryl group” is a “substituted arylgroup”.) In the description herein, the simple expression “aryl group”encompasses both the “unsubstituted aryl group” and the “substitutedaryl group”.

The “substituted aryl group” means a group formed by substituting one ormore hydrogen atom of the “unsubstituted aryl group” by a substituent.Examples of the “substituted aryl group” include groups formed by one ormore hydrogen atom of each of the “unsubstituted aryl groups” in the setof specific examples G1A by a substituent, and the examples of thesubstituted aryl groups in the set of specific examples G1B. Theexamples of the “unsubstituted aryl group” and the examples of the“substituted aryl group” enumerated herein are mere examples, and the“substituted aryl group” in the description herein encompasses groupsformed by substituting a hydrogen atom bonded to the carbon atom of thearyl group itself of each of the “substituted aryl groups” in the set ofspecific examples G1B by a substituent, and groups formed bysubstituting a hydrogen atom of the substituent of each of the“substituted aryl groups” in the set of specific examples G1B by asubstituent.

Unsubstituted Aryl Group (Set of Specific Examples G1A):

a phenyl group,

a p-biphenyl group,

a m-biphenyl group,

an o-biphenyl group,

a p-terphenyl-4-yl group,

a p-terphenyl-3-yl group,

a p-terphenyl-2-yl group,

a m-terphenyl-4-yl group,

a m-terphenyl-3-yl group,

a m-terphenyl-2-yl group,

an o-terphenyl-4-yl group,

an o-terphenyl-3-yl group,

an o-terphenyl-2-yl group,

a 1-naphthyl group,

a 2-naphthyl group,

an anthryl group,

a benzanthryl group,

a phenanthryl group,

a benzophenanthryl group,

a phenarenyl group,

a pyrenyl group,

a chrysenyl group,

a benzochrysenyl group,

a triphenylenyl group,

a benzotriphenylenyl group,

a tetracenyl group,

a pentacenyl group,

a fluorenyl group,

a 9,9′-spirobifluorenyl group,

a benzofluorenyl group,

a dibenzofluorenyl group,

a fluoranthenyl group,

a benzofluoranthenyl group,

a perylenyl group, and

monovalent aryl groups derived by removing one hydrogen atom from eachof the ring structures represented by the following general formulae(TEMP-1) to (TEMP-15):

Substituted Aryl Group (Set of Specific Examples G1B):

an o-tolyl group,

a m-tolyl group,

a p-tolyl group,

a p-xylyl group,

a m-xylyl group,

an o-xylyl group,

a p-isopropylphenyl group,

a m-isopropylphenyl group,

an o-isopropylphenyl group,

a p-t-butylphenyl group,

a m-t-butylphenyl group,

a o-t-butylphenyl group,

a 3,4,5-trimethylphenyl group,

a 9,9-dimethylfluorenyl group,

a 9,9-diphenylfluorenyl group,

a 9,9-bis(4-methylphenyl)fluorenyl group,

a 9,9-bis(4-isopropylphenyl)fluorenyl group,

a 9,9-bis(4-t-butylphenyl)fluorenyl group,

a cyanophenyl group,

a triphenylsilylphenyl group,

a trimethylsilylphenyl group,

a phenylnaphthyl group,

a naphthylphenyl group, and

groups formed by substituting one or more hydrogen atom of each ofmonovalent aryl groups derived from the ring structures represented bythe general formulae (TEMP-1) to (TEMP-15) by a substituent.

Substituted or Unsubstituted Heterocyclic Group

In the description herein, the “heterocyclic group” means a cyclic groupcontaining at least one hetero atom in the ring atoms. Specific examplesof the hetero atom include a nitrogen atom, an oxygen atom, a sulfuratom, a silicon atom, a phosphorus atom, and a boron atom.

In the description herein, the “heterocyclic group” is a monocyclicgroup or a condensed ring group.

In the description herein, the “heterocyclic group” is an aromaticheterocyclic group or a non-aromatic heterocyclic group.

In the description herein, specific examples (set of specific examplesG2) of the “substituted or unsubstituted heterocyclic group” include theunsubstituted heterocyclic groups (set of specific examples G2A) and thesubstituted heterocyclic groups (set of specific examples G2B) shownbelow. (Herein, the unsubstituted heterocyclic group means the casewhere the “substituted or unsubstituted heterocyclic group” is an“unsubstituted heterocyclic group”, and the substituted heterocyclicgroup means the case where the “substituted or unsubstitutedheterocyclic group” is a “substituted heterocyclic group”.) In thedescription herein, the simple expression “heterocyclic group”encompasses both the “unsubstituted heterocyclic group” and the“substituted heterocyclic group”.

The “substituted heterocyclic group” means a group formed bysubstituting one or more hydrogen atom of the “unsubstitutedheterocyclic group” by a substituent. Specific examples of the“substituted heterocyclic group” include groups formed by substituting ahydrogen atom of each of the “unsubstituted heterocyclic groups” in theset of specific examples G2A by a substituent, and the examples of thesubstituted heterocyclic groups in the set of specific examples G2B. Theexamples of the “unsubstituted heterocyclic group” and the examples ofthe “substituted heterocyclic group” enumerated herein are mereexamples, and the “substituted heterocyclic group” in the descriptionherein encompasses groups formed by substituting a hydrogen atom bondedto the ring atom of the heterocyclic group itself of each of the“substituted heterocyclic groups” in the set of specific examples G2B bya substituent, and groups formed by substituting a hydrogen atom of thesubstituent of each of the “substituted heterocyclic groups” in the setof specific examples G2B by a substituent.

The set of specific examples G2A includes, for example, theunsubstituted heterocyclic group containing a nitrogen atom (set ofspecific examples G2A1), the unsubstituted heterocyclic group containingan oxygen atom (set of specific examples G2A2), the unsubstitutedheterocyclic group containing a sulfur atom (set of specific examplesG2A3), and monovalent heterocyclic groups derived by removing onehydrogen atom from each of the ring structures represented by thefollowing general formulae (TEMP-16) to (TEMP-33) (set of specificexamples G2A4).

The set of specific examples G2B includes, for example, the substitutedheterocyclic groups containing a nitrogen atom (set of specific examplesG2B1), the substituted heterocyclic groups containing an oxygen atom(set of specific examples G2B2), the substituted heterocyclic groupscontaining a sulfur atom (set of specific examples G2B3), and groupsformed by substituting one or more hydrogen atom of each of monovalentheterocyclic groups derived from the ring structures represented by thefollowing general formulae (TEMP-16) to (TEMP-33) by a substituent (setof specific examples G2B4).

Unsubstituted Heterocyclic Group Containing Nitrogen Atom (Set ofSpecific Examples G2A1):

a pyrrolyl group,

an imidazolyl group,

a pyrazolyl group,

a triazolyl group,

a tetrazolyl group,

an oxazolyl group,

an isoxazolyl group,

an oxadiazolyl group,

a thiazolyl group,

an isothiazolyl group,

a thiadiazolyl group,

a pyridyl group,

a pyridazinyl group,

a pyrimidinyl group,

a pyrazinyl group,

a triazinyl group,

an indolyl group,

an isoindolyl group,

an indolizinyl group,

a quinolizinyl group,

a quinolyl group,

an isoquinolyl group,

a cinnolinyl group,

a phthalazinyl group,

a quinazolinyl group,

a quinoxalinyl group,

a benzimidazolyl group,

an indazolyl group,

a phenanthrolinyl group,

a phenanthridinyl group,

an acridinyl group,

a phenazinyl group,

a carbazolyl group,

a benzocarbazolyl group,

a morpholino group,

a phenoxazinyl group,

a phenothiazinyl group,

an azacarbazolyl group, and

a diazacarbazolyl group.

Unsubstituted Heterocyclic Group Containing Oxygen Atom (Set of SpecificExamples G2A2):

a furyl group,

an oxazolyl group,

an isoxazolyl group,

an oxadiazolyl group,

a xanthenyl group,

a benzofuranyl group,

an isobenzofuranyl group,

a dibenzofuranyl group,

a naphthobenzofuranyl group,

a benzoxazolyl group,

a benzisoxazolyl group,

a phenoxazinyl group,

a morpholino group,

a dinaphthofuranyl group,

an azadibenzofuranyl group,

a diazadibenzofuranyl group,

an azanaphthobenzofuranyl group, and

a diazanaphthobenzofuranyl group.

Unsubstituted Heterocyclic Group Containing Sulfur Atom (Set of SpecificExamples G2A3):

a thienyl group,

a thiazolyl group,

an isothiazolyl group,

a thiadiazolyl group,

a benzothiophenyl group (benzothienyl group),

an isobenzothiophenyl group (isobenzothienyl group),

a dibenzothiophenyl group (dibenzothienyl group),

a naphthobenzothiophenyl group (naphthobenzothienyl group),

a benzothiazolyl group,

a benzisothiazolyl group,

a phenothiazinyl group,

a dinaphthothiophenyl group (dinaphthothienyl group),

an azadibenzothiophenyl group (azadibenzothienyl group),

a diazadibenzothiophenyl group (diazadibenzothienyl group),

an azanaphthobenzothiophenyl group (azanaphthobenzothienyl group), and

a diazanaphthobenzothiophenyl group (diazanaphthobenzothienyl group).

Monovalent Heterocyclic Group Derived by Removing One Hydrogen Atom fromRing Structures Represented by General Formulae (TEMP-16) to (TEMP-33)(Set of Specific Examples G2A4)

In the general formulae (TEMP-16) to (TEMP-33), X_(A) and Y_(A) eachindependently represent an oxygen atom, a sulfur atom, NH, or CH₂,provided that at least one of X_(A) and Y_(A) represents an oxygen atom,a sulfur atom, or NH.

In the general formulae (TEMP-16) to (TEMP-33), in the case where atleast one of X_(A) and Y_(A) represents NH or CH₂, the monovalentheterocyclic groups derived from the ring structures represented by thegeneral formulae (TEMP-16) to (TEMP-33) include monovalent groups formedby removing one hydrogen atom from the NH or CH₂.

Substituted Heterocyclic Group Containing Nitrogen Atom (Set of SpecificExamples G2B1):

a (9-phenyl)carbazolyl group,

a (9-biphenylyl)carbazolyl group,

a (9-phenyl)phenylcarbazolyl group,

a (9-naphthyl)carbazolyl group,

a diphenylcarbazol-9-yl group,

a phenylcarbazol-9-yl group,

a methylbenzimidazolyl group,

an ethylbenzimidazolyl group,

a phenyltriazinyl group,

a biphenyltriazinyl group,

a diphenyltriazinyl group,

a phenylquinazolinyl group, and

a biphenylquinazolinyl group.

Substituted Heterocyclic Group Containing Oxygen Atom (Set of SpecificExamples G2B2):

a phenyldibenzofuranyl group,

a methyldibenzofuranyl group,

a t-butyldibenzofuranyl group, and

a monovalent residual group of spiro[9H-xanthene-9,9′-[9H]fluorene].

Substituted Heterocyclic Group Containing Sulfur Atom (Set of SpecificExamples G2B3):

a phenyldibenzothiophenyl group,

a methyldibenzothiophenyl group,

a t-butyldibenzothiophenyl group, and

a monovalent residual group of spiro[9H-thioxanthene-9,9′-[9H]fluorene].

Group Formed by Substituting One or More Hydrogen Atom of MonovalentHeterocyclic Group Derived from Ring Structures Represented by GeneralFormulae (TEMP-16) to (TEMP-33) by Substituent (Set of Specific ExamplesG2B4)

The “one or more hydrogen atom of the monovalent heterocyclic group”means one or more hydrogen atom selected from the hydrogen atom bondedto the ring carbon atom of the monovalent heterocyclic group, thehydrogen atom bonded to the nitrogen atom in the case where at least oneof X_(A) and Y_(A) represents NH, and the hydrogen atom of the methylenegroup in the case where one of X_(A) and Y_(A) represents CH₂.

Substituted or Unsubstituted Alkyl Group

In the description herein, specific examples (set of specific examplesG3) of the “substituted or unsubstituted alkyl group” include theunsubstituted alkyl groups (set of specific examples G3A) and thesubstituted alkyl groups (set of specific examples G3B) shown below.(Herein, the unsubstituted alkyl group means the case where the“substituted or unsubstituted alkyl group” is an “unsubstituted alkylgroup”, and the substituted alkyl group means the case where the“substituted or unsubstituted alkyl group” is a “substituted alkylgroup”.) In the description herein, the simple expression “alkyl group”encompasses both the “unsubstituted alkyl group” and the “substitutedalkyl group”.

The “substituted alkyl group” means a group formed by substituting oneor more hydrogen atom of the “unsubstituted alkyl group” by asubstituent. Specific examples of the “substituted alkyl group” includegroups formed by substituting one or more hydrogen atom of each of the“unsubstituted alkyl groups” (set of specific examples G3A) by asubstituent, and the examples of the substituted alkyl groups (set ofspecific examples G3B). In the description herein, the alkyl group inthe “unsubstituted alkyl group” means a chain-like alkyl group.Accordingly, the “unsubstituted alkyl group” encompasses an“unsubstituted linear alkyl group” and an “unsubstituted branched alkylgroup”. The examples of the “unsubstituted alkyl group” and the examplesof the “substituted alkyl group” enumerated herein are mere examples,and the “substituted alkyl group” in the description herein encompassesgroups formed by substituting a hydrogen atom of the alkyl group itselfof each of the “substituted alkyl groups” in the set of specificexamples G3B by a substituent, and groups formed by substituting ahydrogen atom of the substituent of each of the “substituted alkylgroups” in the set of specific examples G3B by a substituent.

Unsubstituted Alkyl Group (Set of Specific Examples G3A):

a methyl group,

an ethyl group,

a n-propyl group,

an isopropyl group,

a n-butyl group,

an isobutyl group,

a s-butyl group, and

a t-butyl group.

Substituted Alkyl Group (Set of Specific Examples G3B):

a heptafluoropropyl group (including isomers),

a pentafluoroethyl group,

a 2,2,2-trifluoroethyl group, and

a trifluoromethyl group.

Substituted or Unsubstituted Alkenyl Group

In the description herein, specific examples (set of specific examplesG4) of the “substituted or unsubstituted alkenyl group” include theunsubstituted alkenyl groups (set of specific examples G4A) and thesubstituted alkenyl groups (set of specific examples G4B) shown below.(Herein, the unsubstituted alkenyl group means the case where the“substituted or unsubstituted alkenyl group” is an “unsubstitutedalkenyl group”, and the substituted alkenyl group means the case wherethe “substituted or unsubstituted alkenyl group” is a “substitutedalkenyl group”.) In the description herein, the simple expression“alkenyl group” encompasses both the “unsubstituted alkenyl group” andthe “substituted alkenyl group”.

The “substituted alkenyl group” means a group formed by substituting oneor more hydrogen atom of the “unsubstituted alkenyl group” by asubstituent. Specific examples of the “substituted alkenyl group”include the “unsubstituted alkenyl groups” (set of specific examplesG4A) that each have a substituent, and the examples of the substitutedalkenyl groups (set of specific examples G4B). The examples of the“unsubstituted alkenyl group” and the examples of the “substitutedalkenyl group” enumerated herein are mere examples, and the “substitutedalkenyl group” in the description herein encompasses groups formed bysubstituting a hydrogen atom of the alkenyl group itself of each of the“substituted alkenyl groups” in the set of specific examples G4B by asubstituent, and groups formed by substituting a hydrogen atom of thesubstituent of each of the “substituted alkenyl groups” in the set ofspecific examples G4B by a substituent.

Unsubstituted Alkenyl Group (Set of Specific Examples G4A):

a vinyl group,

an allyl group,

a 1-butenyl group,

a 2-butenyl group, and

a 3-butenyl group.

Substituted Alkenyl Group (Set of Specific Examples G4B):

a 1,3-butanedienyl group,

a 1-methylvinyl group,

a 1-methylallyl group,

a 1,1-dimethylallyl group,

a 2-methylallyl group, and

a 1,2-dimethylallyl group.

Substituted or Unsubstituted Alkynyl Group

In the description herein, specific examples (set of specific examplesG5) of the “substituted or unsubstituted alkynyl group” include theunsubstituted alkynyl group (set of specific examples G5A) shown below.(Herein, the unsubstituted alkynyl group means the case where the“substituted or unsubstituted alkynyl group” is an “unsubstitutedalkynyl group”.) In the description herein, the simple expression“alkynyl group” encompasses both the “unsubstituted alkynyl group” andthe “substituted alkynyl group”.

The “substituted alkynyl group” means a group formed by substituting oneor more hydrogen atom of the “unsubstituted alkynyl group” by asubstituent. Specific examples of the “substituted alkenyl group”include groups formed by substituting one or more hydrogen atom of the“unsubstituted alkynyl group” (set of specific examples G5A) by asubstituent.

Unsubstituted Alkynyl Group (Set of Specific Examples G5A):

an ethynyl group.

Substituted or Unsubstituted Cycloalkyl Group

In the description herein, specific examples (set of specific examplesG6) of the “substituted or unsubstituted cycloalkyl group” include theunsubstituted cycloalkyl groups (set of specific examples G6A) and thesubstituted cycloalkyl group (set of specific examples G6B) shown below.(Herein, the unsubstituted cycloalkyl group means the case where the“substituted or unsubstituted cycloalkyl group” is an “unsubstitutedcycloalkyl group”, and the substituted cycloalkyl group means the casewhere the “substituted or unsubstituted cycloalkyl group” is a“substituted cycloalkyl group”.) In the description herein, the simpleexpression “cycloalkyl group” encompasses both the “unsubstitutedcycloalkyl group” and the “substituted cycloalkyl group”.

The “substituted cycloalkyl group” means a group formed by substitutingone or more hydrogen atom of the “unsubstituted cycloalkyl group” by asubstituent. Specific examples of the “substituted cycloalkyl group”include groups formed by substituting one or more hydrogen atom of eachof the “unsubstituted cycloalkyl groups” (set of specific examples G6A)by a substituent, and the example of the substituted cycloalkyl group(set of specific examples G6B). The examples of the “unsubstitutedcycloalkyl group” and the examples of the “substituted cycloalkyl group”enumerated herein are mere examples, and the “substituted cycloalkylgroup” in the description herein encompasses groups formed bysubstituting one or more hydrogen atom bonded to the carbon atoms of thecycloalkyl group itself of the “substituted cycloalkyl group” in the setof specific examples G6B by a substituent, and groups formed bysubstituting a hydrogen atom of the substituent of the “substitutedcycloalkyl group” in the set of specific examples G6B by a substituent.

Unsubstituted Cycloalkyl Group (Set of Specific Examples G6A):

a cyclopropyl group,

a cyclobutyl group,

a cyclopentyl group,

a cyclohexyl group,

a 1-adamantyl group,

a 2-adamantyl group,

a 1-norbornyl group, and

a 2-norbornyl group.

Substituted Cycloalkyl Group (Set of Specific Examples G6B):

a 4-methylcyclohexyl group.

Group Represented by —Si(R₉₀₁)(R₉₀₂)(R₉₀₃)

In the description herein, specific examples (set of specific examplesG7) of the group represented by —Si(R₉₀₁)(R₉₀₂)(R₉₀₃) include:

—Si(G1)(G1)(G1),

—Si(G1)(G2)(G2),

—Si(G1)(G1)(G2),

—Si(G2)(G2)(G2),

—Si(G3)(G3)(G3), and

—Si(G6)(G6)(G6).

Herein,

G1 represents the “substituted or unsubstituted aryl group” described inthe set of specific examples G1,

G2 represents the “substituted or unsubstituted heterocyclic group”described in the set of specific examples G2,

G3 represents the “substituted or unsubstituted alkyl group” describedin the set of specific examples G3, and

G6 represents the “substituted or unsubstituted cycloalkyl group”described in the set of specific examples G6.

Plural groups represented by G1 in —Si(G1)(G1)(G1) are the same as ordifferent from each other.

Plural groups represented by G2 in —Si(G1)(G2)(G2) are the same as ordifferent from each other.

Plural groups represented by G1 in —Si(G1)(G1)(G2) are the same as ordifferent from each other.

Plural groups represented by G2 in —Si(G2)(G2)(G2) are the same as ordifferent from each other.

Plural groups represented by G3 in —Si(G3)(G3)(G3) are the same as ordifferent from each other.

Plural groups represented by G6 in —Si(G6)(G6)(G6) are the same as ordifferent from each other.

Group Represented by —O—(R₉₀₄)

In the description herein, specific examples (set of specific examplesG8) of the group represented by —O—(R₉₀₄) include:

—O(G1),

—O(G2),

—O(G3), and

—O(G6).

Herein,

G1 represents the “substituted or unsubstituted aryl group” described inthe set of specific examples G1,

G2 represents the “substituted or unsubstituted heterocyclic group”described in the set of specific examples G2,

G3 represents the “substituted or unsubstituted alkyl group” describedin the set of specific examples G3, and

G6 represents the “substituted or unsubstituted cycloalkyl group”described in the set of specific examples G6.

Group Represented by —S—(R₉₀₅)

In the description herein, specific examples (set of specific examplesG9) of the group represented by —S—(R₉₀₅) include:

—S(G1),

—S(G2),

—S(G3), and

—S(G6).

Herein,

G1 represents the “substituted or unsubstituted aryl group” described inthe set of specific examples G1,

G2 represents the “substituted or unsubstituted heterocyclic group”described in the set of specific examples G2,

G3 represents the “substituted or unsubstituted alkyl group” describedin the set of specific examples G3, and

G6 represents the “substituted or unsubstituted cycloalkyl group”described in the set of specific examples G6.

Group Represented by —N(R₉₀₆)(R₉₀₇)

In the description herein, specific examples (set of specific examplesG10) of the group represented by —N(R₉₀₆)(R₉₀₇) include:

—N(G1)(G1),

—N(G2)(G2),

—N(G1)(G2),

—N(G3)(G3), and

—N(G6)(G6).

G1 represents the “substituted or unsubstituted aryl group” described inthe set of specific examples G1,

G2 represents the “substituted or unsubstituted heterocyclic group”described in the set of specific examples G2,

G3 represents the “substituted or unsubstituted alkyl group” describedin the set of specific examples G3, and

G6 represents the “substituted or unsubstituted cycloalkyl group”described in the set of specific examples G6.

Plural groups represented by G1 in —N(G1)(G1) are the same as ordifferent from each other.

Plural groups represented by G2 in —N(G2)(G2) are the same as ordifferent from each other.

Plural groups represented by G3 in —N(G3)(G3) are the same as ordifferent from each other.

Plural groups represented by G6 in —N(G6)(G6) are the same as ordifferent from each other.

Halogen Atom

In the description herein, specific examples (set of specific examplesG11) of the “halogen atom” include a fluorine atom, a chlorine atom, abromine atom, and an iodine atom.

Substituted or Unsubstituted Fluoroalkyl Group

In the description herein, the “substituted or unsubstituted fluoroalkylgroup” means a group formed by substituting at least one hydrogen atombonded to the carbon atom constituting the alkyl group in the“substituted or unsubstituted alkyl group” by a fluorine atom, andencompasses a group formed by substituting all the hydrogen atoms bondedto the carbon atoms constituting the alkyl group in the “substituted orunsubstituted alkyl group” by fluorine atoms (i.e., a perfluoroalkylgroup). The number of carbon atoms of the “unsubstituted fluoroalkylgroup” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18,unless otherwise indicated in the description. The “substitutedfluoroalkyl group” means a group formed by substituting one or morehydrogen atom of the “fluoroalkyl group” by a substituent. In thedescription herein, the “substituted fluoroalkyl group” encompasses agroup formed by substituting one or more hydrogen atom bonded to thecarbon atom of the alkyl chain in the “substituted fluoroalkyl group” bya substituent, and a group formed by substituting one or more hydrogenatom of the substituent in the “substituted fluoroalkyl group” by asubstituent. Specific examples of the “unsubstituted fluoroalkyl group”include examples of groups formed by substituting one or more hydrogenatom in each of the “alkyl group” (set of specific examples G3) by afluorine atom.

Substituted or Unsubstituted Haloalkyl Group

In the description herein, the “substituted or unsubstituted haloalkylgroup” means a group formed by substituting at least one hydrogen atombonded to the carbon atom constituting the alkyl group in the“substituted or unsubstituted alkyl group” by a halogen atom, andencompasses a group formed by substituting all the hydrogen atoms bondedto the carbon atoms constituting the alkyl group in the “substituted orunsubstituted alkyl group” by halogen atoms. The number of carbon atomsof the “unsubstituted haloalkyl group” is 1 to 50, preferably 1 to 30,and more preferably 1 to 18, unless otherwise indicated in thedescription. The “substituted haloalkyl group” means a group formed bysubstituting one or more hydrogen atom of the “haloalkyl group” by asubstituent. In the description herein, the “substituted haloalkylgroup” encompasses a group formed by substituting one or more hydrogenatom bonded to the carbon atom of the alkyl chain in the “substitutedhaloalkyl group” by a substituent, and a group formed by substitutingone or more hydrogen atom of the substituent in the “substitutedhaloalkyl group” by a substituent. Specific examples of the“unsubstituted haloalkyl group” include examples of groups formed bysubstituting one or more hydrogen atom in each of the “alkyl group” (setof specific examples G3) by a halogen atom. A haloalkyl group may bereferred to as a halogenated alkyl group in some cases.

Substituted or Unsubstituted Alkoxy Group

In the description herein, specific examples of the “substituted orunsubstituted alkoxy group” include a group represented by —O(G3),wherein G3 represents the “substituted or unsubstituted alkyl group”described in the set of specific examples G3. The number of carbon atomsof the “unsubstituted alkoxy group” is 1 to 50, preferably 1 to 30, andmore preferably 1 to 18, unless otherwise indicated in the description.

Substituted or Unsubstituted Alkylthio Group

In the description herein, specific examples of the “substituted orunsubstituted alkylthio group” include a group represented by —S(G3),wherein G3 represents the “substituted or unsubstituted alkyl group”described in the set of specific examples G3. The number of carbon atomsof the “unsubstituted alkylthio group” is 1 to 50, preferably 1 to 30,and more preferably 1 to 18, unless otherwise indicated in thedescription.

Substituted or Unsubstituted Aryloxy Group

In the description herein, specific examples of the “substituted orunsubstituted aryloxy group” include a group represented by —O(G1),wherein G1 represents the “substituted or unsubstituted aryl group”described in the set of specific examples G1. The number of ring carbonatoms of the “unsubstituted aryloxy group” is 6 to 50, preferably 6 to30, and more preferably 6 to 18, unless otherwise indicated in thedescription.

Substituted or Unsubstituted Arylthio Group

In the description herein, specific examples of the “substituted orunsubstituted arylthio group” include a group represented by —S(G1),wherein G1 represents the “substituted or unsubstituted aryl group”described in the set of specific examples G1. The number of ring carbonatoms of the “unsubstituted arylthio group” is 6 to 50, preferably 6 to30, and more preferably 6 to 18, unless otherwise indicated in thedescription.

Substituted or Unsubstituted Trialkylsilyl Group

In the description herein, specific examples of the “trialkylsilylgroup” include a group represented by —Si(G3)(G3)(G3), wherein G3represents the “substituted or unsubstituted alkyl group” described inthe set of specific examples G3. Plural groups represented by G3 in—Si(G3)(G3)(G3) are the same as or different from each other. The numberof carbon atoms of each of alkyl groups of the “substituted orunsubstituted trialkylsilyl group” is 1 to 50, preferably 1 to 20, andmore preferably 1 to 6, unless otherwise indicated in the description.

Substituted or Unsubstituted Aralkyl Group

In the description herein, specific examples of the “substituted orunsubstituted aralkyl group” include a group represented by -(G3)-(G1),wherein G3 represents the “substituted or unsubstituted alkyl group”described in the set of specific examples G3, and G1 represents the“substituted or unsubstituted aryl group” described in the set ofspecific examples G1. Accordingly, the “aralkyl group” is a group formedby substituting a hydrogen atom of an “alkyl group” by an “aryl group”as a substituent, and is one embodiment of the “substituted alkylgroup”. The “unsubstituted aralkyl group” is an “unsubstituted alkylgroup” that is substituted by an “unsubstituted aryl group”, and thenumber of carbon atoms of the “unsubstituted aralkyl group” is 7 to 50,preferably 7 to 30, and more preferably 7 to 18, unless otherwiseindicated in the description.

Specific examples of the “substituted or unsubstituted aralkyl group”include a benzyl group, a 1-phenylethyl group, a 2-phenylethyl group, a1-phenylisopropyl group, a 2-phenylisopropyl group, a phenyl-t-butylgroup, an α-naphthylmethyl group, a 1-α-naphthylethyl group, a2-α-naphthylethyl group, a 1-α-naphthylisopropyl group, a2-α-naphthylisopropyl group, a β-naphthylmethyl group, a1-β-naphthylethyl group, a 2-β-naphthylethyl group, a1-β-naphthylisopropyl group, and a 2-β-naphthylisopropyl group.

In the description herein, the substituted or unsubstituted aryl groupis preferably a phenyl group, a p-biphenyl group, a m-biphenyl group, ano-biphenyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, ap-terphenyl-2-yl group, a m-terphenyl-4-yl group, a m-terphenyl-3-ylgroup, a m-terphenyl-2-yl group, an o-terphenyl-4-yl group, ano-terphenyl-3-yl group, an o-terphenyl-2-yl group, a 1-naphthyl group, a2-naphthyl group, an anthryl group, a phenanthryl group, a pyrenylgroup, a chrysenyl group, a triphenylenyl group, a fluorenyl group, a9,9′-spirobifluorenyl group, a 9,9-dimethylfluorenyl group, a9,9-diphenylfluorenyl group, and the like, unless otherwise indicated inthe description.

In the description herein, the substituted or unsubstituted heterocyclicgroup is preferably a pyridyl group, a pyrimidinyl group, a triazinylgroup, a quinolyl group, an isoquinolyl group, a quinazolinyl group, abenzimidazolyl group, a phenanthrolinyl group, a carbazolyl group (e.g.,a 1-carbazolyl, group, a 2-carbazolyl, group, a 3-carbazolyl, group, a4-carbazolyl, group, or a 9-carbazolyl, group), a benzocarbazolyl group,an azacarbazolyl group, a diazacarbazolyl group, a dibenzofuranyl group,a naphthobenzofuranly group, an azadibenzofuranyl group, adiazadibenzofuranyl group, a dibenzothiophenyl group, anaphthobenzothiophenyl group, an azadibenzothiophenyl group, adiazadibenzothiophenyl group, a (9-phenyl)carbazolyl group (e.g., a(9-phenyl)carbazol-1-yl group, a (9-phenyl)carbazol-2-yl group, a(9-phenyl)carbazol-3-yl group, or a (9-phenyl)carbazol-4-yl group), a(9-biphenylyl)carbazolyl group, a (9-phenyl)phenylcarbazolyl group, adiphenylcarbazol-9-yl group, a phenylcarbazol-9-yl group, aphenyltriazinyl group, a biphenylyltriazinyl group, a diphenyltriazinylgroup, a phenyldibenzofuranyl group, a phenyldibenzothiophenyl group,and the like, unless otherwise indicated in the description.

In the description herein, the carbazolyl group is specifically any oneof the following groups unless otherwise indicated in the description.

In the description herein, the (9-phenyl)carbazolyl group isspecifically any one of the following groups unless otherwise indicatedin the description.

In the general formulae (TEMP-Cz1) to (TEMP-Cz9), * represents a bondingsite.

In the description herein, the dibenzofuranyl group and thedibenzothiophenyl group are specifically any one of the following groupsunless otherwise indicated in the description.

In the general formulae (TEMP-34) to (TEMP-41), * represents a bondingsite.

In the description herein, the substituted or unsubstituted alkyl groupis preferably a methyl group, an ethyl group, a propyl group, anisopropyl group, a n-butyl group, an isobutyl group, a t-butyl group, orthe like unless otherwise indicated in the description.

Substituted or Unsubstituted Arylene Group In the description herein,the “substituted or unsubstituted arylene group” is a divalent groupderived by removing one hydrogen atom on the aryl ring from the“substituted or unsubstituted aryl group” described above unlessotherwise indicated in the description. Specific examples (set ofspecific examples G12) of the “substituted or unsubstituted arylenegroup” include divalent groups derived by removing one hydrogen atom onthe aryl ring from the “substituted or unsubstituted aryl groups”described in the set of specific examples G1.

Substituted or Unsubstituted Divalent Heterocyclic Group

In the description herein, the “substituted or unsubstituted divalentheterocyclic group” is a divalent group derived by removing one hydrogenatom on the heterocyclic ring from the “substituted or unsubstitutedheterocyclic group” described above unless otherwise indicated in thedescription. Specific examples (set of specific examples G13) of the“substituted or unsubstituted divalent heterocyclic group” includedivalent groups derived by removing one hydrogen atom on theheterocyclic ring from the “substituted or unsubstituted heterocyclicgroups” described in the set of specific examples G2.

Substituted or Unsubstituted Alkylene Group

In the description herein, the “substituted or unsubstituted alkylenegroup” is a divalent group derived by removing one hydrogen atom on thealkyl chain from the “substituted or unsubstituted alkyl group”described above unless otherwise indicated in the description. Specificexamples (set of specific examples G14) of the “substituted orunsubstituted alkylene group” include divalent groups derived byremoving one hydrogen atom on the alkyl chain from the “substituted orunsubstituted alkyl groups” described in the set of specific examplesG3.

In the description herein, the substituted or unsubstituted arylenegroup is preferably any one of the groups represented by the followinggeneral formulae (TEMP-42) to (TEMP-68) unless otherwise indicated inthe description.

In the general formulae (TEMP-42) to (TEMP-52), Q₁ to Q₁₀ eachindependently represent a hydrogen atom or a substituent.

In the general formulae (TEMP-42) to (TEMP-52), * represents a bondingsite.

In the general formulae (TEMP-53) to (TEMP-62), Q₁ to Q₁₀ eachindependently represent a hydrogen atom or a substituent.

The formulae Q₉ and Q₁₀ may be bonded to each other to form a ring via asingle bond.

In the general formulae (TEMP-53) to (TEMP-62), * represents a bondingsite.

In the general formulae (TEMP-63) to (TEMP-68), Q₁ to Q₈ eachindependently represent a hydrogen atom or a substituent.

In the general formulae (TEMP-63) to (TEMP-68), * represents a bondingsite.

In the description herein, the substituted or unsubstituted divalentheterocyclic group is preferably the groups represented by the followinggeneral formulae (TEMP-69) to (TEMP-102) unless otherwise indicated inthe description.

In the general formulae (TEMP-69) to (TEMP-82), Q₁ to Q₉ eachindependently represent a hydrogen atom or a substituent.

In the general formulae (TEMP-83) to (TEMP-102), Q₁ to Q₈ eachindependently represent a hydrogen atom or a substituent.

The above are the explanation of the “substituents in the descriptionherein”.

Case Forming Ring by Bonding

In the description herein, the case where “one or more combinations ofcombinations each including adjacent two or more each are bonded to eachother to form a substituted or unsubstituted monocyclic ring, or eachare bonded to each other to form a substituted or unsubstitutedcondensed ring, or each are not bonded to each other” means a case where“one or more combinations of combinations each including adjacent two ormore each are bonded to each other to form a substituted orunsubstituted monocyclic ring”, a case where “one or more combinationsof combinations each including adjacent two or more each are bonded toeach other to form a substituted or unsubstituted condensed ring”, and acase where “one or more combinations of combinations each includingadjacent two or more each are not bonded to each other”.

In the description herein, the case where “one or more combinations ofcombinations each including adjacent two or more each are bonded to eachother to form a substituted or unsubstituted monocyclic ring” and thecase where “one or more combinations of combinations each includingadjacent two or more each are bonded to each other to form a substitutedor unsubstituted condensed ring” (which may be hereinafter collectivelyreferred to as a “case forming a ring by bonding”) will be explainedbelow. The cases will be explained for the anthracene compoundrepresented by the following general formula (TEMP-103) having ananthracene core skeleton as an example.

For example, in the case where “one or more combinations of combinationseach including adjacent two or more each are bonded to each other toform a ring” among R₉₂₁ to R₉₃₀, the combinations each includingadjacent two as one combination include a combination of R₉₂₁ and R₉₂₂,a combination of R₉₂₂ and R₉₂₃, a combination of R₉₂₃ and R₉₂₄, acombination of R₉₂₄ and R₉₃₀, a combination of R₉₃₀ and R₉₂₅, acombination of R₉₂₅ and R₉₂₆, a combination of R₉₂₆ and R₉₂₇, acombination of R₉₂₇ and R₉₂₈, a combination of R₉₂₈ and R₉₂₉, and acombination of R₉₂₉ and R₉₂₁.

The “one or more combinations” mean that two or more combinations eachincluding adjacent two or more may form rings simultaneously. Forexample, in the case where R₉₂₁ and R₉₂₂ are bonded to each other toform a ring Q_(A), and simultaneously R₉₂₅ and R₉₂₆ are bonded to eachother to form a ring Q_(B), the anthracene compound represented by thegeneral formula (TEMP-103) is represented by the following generalformula (TEMP-104).

The case where the “combination including adjacent two or more formsrings” encompasses not only the case where adjacent two included in thecombination are bonded as in the aforementioned example, but also thecase where adjacent three or more included in the combination arebonded. For example, this case means that R₉₂₁ and R₉₂₂ are bonded toeach other to form a ring Q_(A), R₉₂₂ and R₉₂₃ are bonded to each otherto form a ring Q_(C), and adjacent three (R₉₂₁, R₉₂₂, and R₉₂₃) includedin the combination are bonded to each other to form rings, which arecondensed to the anthracene core skeleton, and in this case, theanthracene compound represented by the general formula (TEMP-103) isrepresented by the following general formula (TEMP-105). In thefollowing general formula (TEMP-105), the ring Q_(A) and the ring Q_(C)share R₉₂₂.

The formed “monocyclic ring” or “condensed ring” may be a saturated ringor an unsaturated ring in terms of structure of the formed ring itself.In the case where the “one combination including adjacent two” forms a“monocyclic ring” or a “condensed ring”, the “monocyclic ring” or the“condensed ring” may form a saturated ring or an unsaturated ring. Forexample, the ring Q_(A) and the ring Q_(B)formed in the general formula(TEMP-104) each are a “monocyclic ring” or a “condensed ring”. The ringQ_(A) and the ring Q_(C) formed in the general formula (TEMP-105) eachare a “condensed ring”. The ring Q_(A) and the ring Q_(C) in the generalformula (TEMP-105) form a condensed ring through condensation of thering Q_(A) and the ring Q_(C). In the case where the ring Q_(A) in thegeneral formula (TMEP-104) is a benzene ring, the ring Q_(A) is amonocyclic ring. In the case where the ring Q_(A) in the general formula(TMEP-104) is a naphthalene ring, the ring Q_(A) is a condensed ring.

The “unsaturated ring” means an aromatic hydrocarbon ring or an aromaticheterocyclic ring. The “saturated ring” means an aliphatic hydrocarbonring or a non-aromatic heterocyclic ring.

Specific examples of the aromatic hydrocarbon ring include thestructures formed by terminating the groups exemplified as the specificexamples in the set of specific examples G1 with a hydrogen atom.

Specific examples of the aromatic heterocyclic ring include thestructures formed by terminating the aromatic heterocyclic groupsexemplified as the specific examples in the set of specific examples G2with a hydrogen atom.

Specific examples of the aliphatic hydrocarbon ring include thestructures formed by terminating the groups exemplified as the specificexamples in the set of specific examples G6 with a hydrogen atom.

The expression “to form a ring” means that the ring is formed only withthe plural atoms of the core structure or with the plural atoms of thecore structure and one or more arbitrary element. For example, the ringQ_(A) formed by bonding R₉₂₁ and R₉₂₂ each other shown in the generalformula (TEMP-104) means a ring formed with the carbon atom of theanthracene skeleton bonded to R₉₂₁, the carbon atom of the anthraceneskeleton bonded to R₉₂₂, and one or more arbitrary element. As aspecific example, in the case where the ring Q_(A) is formed with R₉₂₁and R₉₂₂, and in the case where a monocyclic unsaturated ring is formedwith the carbon atom of the anthracene skeleton bonded to R₉₂₁, thecarbon atom of the anthracene skeleton bonded to R₉₂₂, and four carbonatoms, the ring formed with R₉₂₁ and R₉₂₂ is a benzene ring.

Herein, the “arbitrary element” is preferably at least one kind of anelement selected from the group consisting of a carbon element, anitrogen element, an oxygen element, and a sulfur element, unlessotherwise indicated in the description. For the arbitrary element (forexample, for a carbon element or a nitrogen element), a bond that doesnot form a ring may be terminated with a hydrogen atom or the like, andmay be substituted by an “arbitrary substituent” described later. In thecase where an arbitrary element other than a carbon element iscontained, the formed ring is a heterocyclic ring.

The number of the “one or more arbitrary element” constituting themonocyclic ring or the condensed ring is preferably 2 or more and 15 orless, more preferably 3 or more and 12 or less, and further preferably 3or more and 5 or less, unless otherwise indicated in the description.

What is preferred between the “monocyclic ring” and the “condensed ring”is the “monocyclic ring” unless otherwise indicated in the description.

What is preferred between the “saturated ring” and the “unsaturatedring” is the “unsaturated ring” unless otherwise indicated in thedescription.

The “monocyclic ring” is preferably a benzene ring unless otherwiseindicated in the description.

The “unsaturated ring” is preferably a benzene ring unless otherwiseindicated in the description.

In the case where the “one or more combinations of combinations eachincluding adjacent two or more” each are “bonded to each other to form asubstituted or unsubstituted monocyclic ring”, or each are “bonded toeach other to form a substituted or unsubstituted condensed ring”, it ispreferred that the one or more combinations of combinations eachincluding adjacent two or more each are bonded to each other to form asubstituted or unsubstituted “unsaturated ring” containing the pluralatoms of the core skeleton and 1 or more and 15 or less at least onekind of an element selected from the group consisting of a carbonelement, a nitrogen element, an oxygen element, and a sulfur element,unless otherwise indicated in the description.

In the case where the “monocyclic ring” or the “condensed ring” has asubstituent, the substituent is, for example, an “arbitrary substituent”described later. In the case where the “monocyclic ring” or the“condensed ring” has a substituent, specific examples of the substituentinclude the substituents explained in the section “Substituents inDescription” described above.

In the case where the “saturated ring” or the “unsaturated ring” has asubstituent, the substituent is, for example, an “arbitrary substituent”described later. In the case where the “monocyclic ring” or the“condensed ring” has a substituent, specific examples of the substituentinclude the substituents explained in the section “Substituents inDescription” described above.

The above are the explanation of the case where “one or morecombinations of combinations each including adjacent two or more” eachare “bonded to each other to form a substituted or unsubstitutedmonocyclic ring”, and the case where “one or more combinations ofcombinations each including adjacent two or more” each are “bonded toeach other to form a substituted or unsubstituted condensed ring” (i.e.,the “case forming a ring by bonding”).

Substituent for “Substituted or Unsubstituted”

In one embodiment in the description herein, the substituent for thecase of “substituted or unsubstituted” (which may be hereinafterreferred to as an “arbitrary substituent”) is, for example, a groupselected from the group consisting of

an unsubstituted alkyl group having 1 to 50 carbon atoms,

an unsubstituted alkenyl group having 2 to 50 carbon atoms,

an unsubstituted alkynyl group having 2 to 50 carbon atoms,

an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

—Si(R₉₀₁)(R₉₀₂)(R₉₀₃),

—O—(R₉₀₄)

—S—(R₉₀₅),

—N(R₉₀₆)((R₉₀₇),

a halogen atom, a cyano group, a nitro group,

an unsubstituted aryl group having 6 to 50 ring carbon atoms, and

an unsubstituted heterocyclic group having 5 to 50 ring atoms,

wherein R₉₀₁ to R₉₀₇ each independently represent

a hydrogen atom,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms

a substituted or unsubstituted cycloalkyl group having 3 to 50 ringcarbon atoms,

a substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ringatoms.

In the case where two or more groups each represented by R₉₀₁ exist, thetwo or more groups each represented by R₉₀₁ are the same as or differentfrom each other,

in the case where two or more groups each represented by R₉₀₂ exist, thetwo or more groups each represented by R₉₀₂ are the same as or differentfrom each other,

in the case where two or more groups each represented by R₉₀₃ exist, thetwo or more groups each represented by R₉₀₃ are the same as or differentfrom each other,

in the case where two or more groups each represented by R₉₀₄ exist, thetwo or more groups each represented by R₉₀₄ are the same as or differentfrom each other,

in the case where two or more groups each represented by R₉₀₅ exist, thetwo or more groups each represented by R₉₀₅ are the same as or differentfrom each other,

in the case where two or more groups each represented by R₉₀₆ exist, thetwo or more groups each represented by R₉₀₆ are the same as or differentfrom each other, and

in the case where two or more groups each represented by R₉₀₇ exist, thetwo or more groups each represented by R₉₀₇ are the same as or differentfrom each other.

In one embodiment, the substituent for the case of “substituted orunsubstituted” may be a group selected from the group consisting of

an alkyl group having 1 to 50 carbon atoms,

an aryl group having 6 to 50 ring carbon atoms, and

a heterocyclic group having 5 to 50 ring atoms.

In one embodiment, the substituent for the case of “substituted orunsubstituted” may be a group selected from the group consisting of

an alkyl group having 1 to 18 carbon atoms,

an aryl group having 6 to 18 ring carbon atoms, and

a heterocyclic group having 5 to 18 ring atoms.

The specific examples of the groups for the arbitrary substituentdescribed above are the specific examples of the substituent describedin the section “Substituents in Description” described above.

In the description herein, the arbitrary adjacent substituents may forma “saturated ring” or an “unsaturated ring”, preferably form asubstituted or unsubstituted saturated 5-membered ring, a substituted orunsubstituted saturated 6-membered ring, a substituted or unsubstitutedunsaturated 5-membered ring, or a substituted or unsubstitutedunsaturated 6-membered ring, and more preferably form a benzene ring,unless otherwise indicated.

In the description herein, the arbitrary substituent may further have asubstituent unless otherwise indicated in the description. Thedefinition of the substituent that the arbitrary substituent further hasmay be the same as the arbitrary substituent.

In the description herein, a numerical range shown by “AA to BB” means arange including the numerical value AA as the former of “AA to BB” asthe lower limit value and the numerical value BB as the latter of “AA toBB” as the upper limit value.

The compound of the present disclosure will be described below.

The compound of the present disclosure is represented by the followingformula (1). In the following description, the compounds of the presentdisclosure represented by the formula (1) and by other formulae to bedescribed below each may be referred simply to as an “inventivecompound”.

The symbols in the formula (1) and the formulae described later will beexplained below. Unless otherwise specifically noted, the same symbolsin the following formulae have the same meanings.

In one embodiment of the present disclosure, Ar¹ and Ar² eachindependently represent a group represented by any of the followingformulae (10) to (14):

R¹¹ to R¹⁵, R²¹ to R²⁶, R⁴¹ to R⁴⁸, R⁵¹ to R⁶² and R⁷¹ to R⁷⁸ eachindependently represent a hydrogen atom, a substituted or unsubstitutedalkyl group having 1 to 50 carbon atoms, a substituted or unsubstitutedcycloalkyl group having 3 to 50 ring carbon atoms, a halogen atom, acyano group, a nitro group, a substituted or unsubstituted aryl grouphaving 6 to 50 ring carbon atoms, or a substituted or unsubstitutedheterocyclic group having 5 to 50 ring atoms.

R³¹ to R³⁵ each independently represent a hydrogen atom, a substitutedor unsubstituted alkyl group having 1 to 50 carbon atoms, a substitutedor unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms, ahalogen atom, a cyano group, a nitro group, an unsubstituted aryl grouphaving 6 to 50 ring carbon atoms, or a substituted or unsubstitutedheterocyclic group having 5 to 50 ring atoms.

X represents an oxygen atom, a sulfur atom, or NR⁸¹, R⁸¹ represents ahydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50carbon atoms, a substituted or unsubstituted aryl group having 6 to 50ring carbon atoms, a substituted or unsubstituted heterocyclic grouphaving 5 to 50 ring atoms.

X is preferably an oxygen atom.

R⁸¹ is preferably a substituted or unsubstituted aryl group having 6 to50 ring carbon atoms, more preferably a substituted or unsubstitutedaryl group having 6 to 30 ring carbon atoms, even more preferably aphenyl group.

However, one selected from R¹¹ to R¹⁵ is a single bond bonding to *c,one selected from R²¹ to R²⁶ is a single bond bonding to *d, the otherone selected from R²¹ to R²⁶ is a single bond bonding to *e, oneselected from R⁴⁵ to R⁴⁸ is a single bond bonding to *f, one selectedfrom R⁵⁹ to R⁶² is a single bond bonding to *g, one selected from R⁷⁵ toR⁷⁸ and R⁸¹ is a single bond bonding to *i, *h bonds to one selectedfrom the carbon atoms *4 to *8.

R⁴⁵ or R⁴⁶ is preferably a single bond bonding to *f, and morepreferably R⁴⁵ is a single bond bonding to *f.

R⁶⁰ or R⁶¹ is preferably a single bond bonding to *g.

In one embodiment of the present disclosure, preferably, R⁷⁵ to R⁷⁸ area single bond bonding to *i, and more preferably R⁷⁵ is a single bondbonding to *i.

In another embodiment of the present disclosure where m is 0 and n is 0or where m is 1 and n is 1, preferably, R⁸¹ is a single bond bonding to*i.

*h preferably bonds to the carbon atom *8.

adjacent two selected from R¹¹ to R¹⁵ that are not a single bond,adjacent two selected from R²¹ to R²⁶ and adjacent two selected from R³¹to R³⁵ that are not a single bond, adjacent two selected from R⁴¹ to R⁴⁸that are not a single bond, adjacent two selected from R⁵¹ to R⁶² thatare not a single bond, and adjacent two selected from R⁷¹ to R⁷⁸ thatare not a single bond do not bond to each other and therefore do notform a cyclic structure.

R¹¹ to R¹⁵ that are not a single bond can be all hydrogen atoms, R²¹ toR²⁶ that are not a single bond can be all hydrogen atoms, R³¹ to R³⁵ canbe all hydrogen atoms, R⁴¹ to R⁴⁸ that are not a single bond can be allhydrogen atoms, R⁵¹ to R⁶² that are not a single bond can be allhydrogen atoms, and R⁷¹ to R⁷⁸ that are not a single bond can be allhydrogen atoms.

** represents a bonding position to the central nitrogen atom, m is 0 or1, n is 0 or 1.

In the formulae (10) to (12) and the formula (14), when m is 0 and n is0, *e bonds to the central nitrogen atom, when m is 0 and n is 1, *cbonds to the central nitrogen atom, and when m is 1 and n is 0, *e bondsto one selected from R¹¹ to R¹⁵.

In the formula (13), when m is 0 and n is 1, *c bonds to the centralnitrogen atom, when m is 1 and n is 0, *e bonds to one selected from R¹¹to R¹⁵, a case where m is 0 and n is 0 is excluded.

In the formula (14), when m is 0 and n is 1, and when m is 1 and n is 0,one selected from R⁷⁵ to R⁷⁸ is a single bond bonding to *i.

In one embodiment of the present disclosure, in the formulae (10) to(12) and the formula (14), m is 0 and n is 0. In another embodiment ofthe present disclosure, in the formulae (10) to (13) and (14), m is 1and n is 1. In still another embodiment, in the formulae (10) to (13)and (14), m is 0 and n is 1. In still another embodiment, in theformulae (10) to (13), m is 0 and n is 1.

The benzene ring A and the benzene ring B, the benzene ring A and thebenzene ring C, the benzene ring B and the benzene ring C, the benzenering A and the naphthalene ring, and the benzene ring B and thenaphthalene ring do not crosslink.

In another embodiment of the present disclosure, Ar¹ is a grouprepresented by the formula (10) or (11), and Ar² is a group representedby any of the formulae (10) to (14).

The group represented by the formula (10) is preferably a substituted orunsubstituted group selected from the following formulae.

wherein arbitrary groups are omitted.

The group represented by the formula (11) is preferably a substituted orunsubstituted group selected from the following formulae.

wherein arbitrary groups are omitted.

The group represented by the formula (12) is preferably a substituted orunsubstituted group selected from the following formula.

wherein arbitrary groups are omitted.

The group represented by the formula (13) is preferably a substituted orunsubstituted group selected from the following formulae.

wherein arbitrary groups are omitted.

In one embodiment of the present disclosure, the group represented bythe formula (14) is preferably a group represented by the followingformula (14-1).

In another embodiment of the present disclosure, the group representedby the formula (14) is preferably a group represented by the followingformula (14-2).

wherein

R¹¹ to R¹⁵, R²¹ to R²⁶, R⁷¹ to R⁷⁸, *c, *d, *e, X, **, m, n, the benzenering A and the benzene ring B are as defined in the formula (1),

one selected from R⁷⁵ to R⁷⁸ is a single bond bonding to *j.

In the formula (14-1), R⁷⁵ is preferably a single bond bonding to *i.

In one embodiment of the present disclosure, the group represented bythe formula (14) is preferably a group represented by the followingformula (14-1-1).

wherein

R¹¹ to R¹⁵, R⁷¹ to R⁷⁸, *c, X, **, m and the benzene ring A are asdefined in the formula (1),

one selected from R⁷⁵ to R⁷⁸ is a single bond bonding to *j.

In the formula (14-1-1), R⁷⁵ is preferably a single bond bonding to *i.

The group represented by the formula (14) is preferably a substituted orunsubstituted group selected from the following formulae.

wherein arbitrary groups are omitted.

Preferably, Ar¹ and Ar² each are independently a group represented byany of the formulae (10), (11) and (14), and more preferably, at leastone of Ar¹ and Ar² is a group represented by the formula (11).

In one embodiment of the present disclosure, in the formula (10),preferably, m is 0 and n is 0, and R³¹ to R³⁵ are hydrogen atoms.

In another embodiment of the present disclosure, in the formula (10),preferably, m is 0 and n is 1, and R³¹ to R³⁵ are hydrogen atoms.

In still another embodiment of the present disclosure, in the formula(10), preferably, m is 0 and n is 1, and R²¹ to R²⁶ that are not asingle bond each are a hydrogen atom or a phenyl group, and R³¹ to R³⁵are hydrogen atoms.

In still another embodiment of the present disclosure, in the formula(10), preferably, m is 1 and n is 0, and R³¹ to R³⁵ are hydrogen atoms.

In still another embodiment of the present disclosure, in the formula(10), preferably, m is 1 and n is 0, and R¹¹ to R¹⁵ that are not asingle bond each are a hydrogen atom or a phenyl group, and R³¹ to R³⁵are hydrogen atoms.

In still another embodiment, in the formula (11), preferably, m is 0 andn is 0.

In still another embodiment, in the formula (11), preferably, m is 0 andn is 1.

In still another embodiment, in the formula (11), preferably, m is 1 andn is 0.

Preferably, Ar¹ and Ar² each are independently a group represented byany of the formulae (20) to (24).

wherein

R¹¹ to R¹⁵, R²¹, R²², R²⁴, R²⁵, R³¹ to R³⁵, R⁴¹ to R⁴⁸, R⁵¹ to R⁶², R⁷¹to R⁷⁸, *f, *g, *h, *i, X, **, m, n, the benzene ring A, the benzenering B and the benzene ring C are as defined in the formula (1).

More preferably, Ar¹ and Ar² each are independently a group representedby the formula (20) or (21).

wherein

R¹¹ to R¹⁵, R²¹, R²², R²⁴, R²⁵, R³¹ to R³⁵, R⁴¹ to R⁴⁸, *, m, n, thebenzene ring A, the benzene ring B and the benzene ring C are as definedin the formula (1).

In one embodiment of the present disclosure, in the formulae (20) to(22) and (24), m is 0 and n is 0. In another embodiment of the presentdisclosure, in the formulae (20) to (24), m is 1 and n is 1. In stillanother embodiment, in the formulae (20) to (24), m is 0 and n is 1.

In one embodiment of the present disclosure, the group represented bythe formula (24) is preferably a group represented by the formula(24-1).

In another embodiment of the present disclosure, the group representedby the formula (24) is preferably a group represented by the formula(24-2).

wherein

R¹¹, R¹², R¹⁴, R¹⁵, R²¹, R²², R²⁴, R²⁵, R⁷¹ to R⁷⁸, X, *, m, n, thebenzene ring A and the benzene ring B are as defined in the formula (1),

one selected from R⁷⁵ to R⁷⁸ is a single bond bonding to *j.

In the formula (24-1), R⁷⁵ is preferably a single bond bonding to *i.

In one embodiment of the present disclosure, the group represented bythe formula (24) is preferably a group represented by the formula(24-1-1).

wherein

R¹¹, R¹², R¹⁴, R¹⁵, R⁷¹ to R⁷⁸, X, **, m, and the benzene ring A are asdefined in the formula (1),

one selected from R⁷⁵ to R⁷⁸ is a single bond bonding to *j.

*a bonds to one selected from the carbon atoms *1 to *3.

*a preferably bonds to the carbon atom *2 or *3, and more preferablybond so *3.

R¹ to R⁴ each independently represent a hydrogen atom, or a substitutedor unsubstituted alkyl group having 1 to 50 carbon atoms.

However, one selected from R¹ to R⁴, preferably R² and R³ are a singlebond bonding to *b.

Adjacent two selected from R¹ to R⁴ that are not a single bond bondingto *b do not bond to each other and therefore do not form a cyclicstructure.

R¹ to R⁴ not a single bond bonding to *b can be all hydrogen atoms.

R⁵ to R⁹ each independently represent a hydrogen atom, a substituted orunsubstituted alkyl group having 1 to 50 carbon atoms, or a substitutedor unsubstituted phenyl group.

However, adjacent two selected from R⁵ to R⁹ each independently may bondto each other to form a substituted or unsubstituted cyclic structure,or may not bond to each other and therefore may not form a cyclicstructure.

In the case where two selected from R⁵ to R⁹ each independently bond toeach other to form a substituted or unsubstituted cyclic structure, thefollowing formulae are preferred.

R⁵ to R⁹ can be all hydrogen atoms.

Preferably, Ar¹ and Ar² each are independently a substituted orunsubstituted group represented by the following formulae.

wherein arbitrary groups are omitted.

Details of the substituted or unsubstituted alkyl group having 1 to 50carbon atoms that are described for the definition of the formulaementioned above are as described in the section of “Substituents inDescription” described above.

The unsubstituted alkyl group is preferably a methyl group, an ethylgroup, an n-propyl group, an isopropyl group, an n-butyl group, anisobutyl group, an s-butyl group, a t-butyl group, or an n-pentyl group,more preferably a methyl group, an ethyl group, an isopropyl group, or at-butyl group, even more preferably a methyl group or a t-butyl group.

Details of the substituted or unsubstituted aryl group having 6 to 50ring carbon atoms that are described for the definition of the formulaementioned above are as described in the section of “Substituents inDescription” described above.

The substituted or unsubstituted aryl group having 6 to 50 ring carbonatoms is preferably selected from a phenyl group, a 1-naphthyl group, a2-naphthyl group, a p-biphenyl group, an m-biphenyl group, an o-biphenylgroup, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, ap-terphenyl-2-yl group, an m-terphenyl-4-yl group, an m-terphenyl-3-ylgroup, an m-terphenyl-2-yl group, an m-terphenyl-3′-yl group, ano-terphenyl-4-yl group, an o-terphenyl-3-yl group and ano-terphenyl-2-yl group.

Details of the arbitrary substituted or unsubstituted cyclic structurethat adjacent two form, as described for the definition of the formulaementioned above, are as described in the section of “Substituents inDescription” described above, and is selected from a substituted orunsubstituted aromatic hydrocarbon ring, a substituted or unsubstitutedaliphatic hydrocarbon ring, a substituted or unsubstituted aromatichetero ring, and a substituted or unsubstituted nonaromatic hetero ring.

Examples of the aromatic hydrocarbon ring include a benzene ring, abiphenylene ring, a naphthalene ring, and a fluorene ring, and anaphthalene ring and a fluorene ring are preferred.

Examples of the aliphatic hydrocarbon ring include a cyclopentene ring,a cyclopentadiene ring, a cyclohexene ring, a cyclohexadiene ring, and ahydrocarbon ring formed by partially hydrogenating the above-mentionedaromatic hydrocarbon ring.

Examples of the aromatic hetero ring include a pyrrole ring, a furanring, a thiophene ring, a pyridine ring, an imidazole ring, a pyrazolering, an indole ring, an isoindole ring, a benzofuran ring, anisobenzofuran ring, a benzothiophene ring, a benzimidazole ring, anindazole ring, a dibenzofuran ring, a naphthobenzofuran ring, adibenzothiophene ring, a naphthobenzothiophene ring, a carbazole ring,and a benzocarbazole ring, and a dibenzofuran ring, a dibenzothiophenering and a carbazole ring are preferred.

Examples of the nonaromatic heterocyclic group include a hetero ringformed by partially hydrogenating the above-mentioned aromatic heteroring.

In the case where the group in the definition of the formulae mentionedabove has an arbitrary substituent, details of the arbitrary substituentexpressed by “substituted or unsubstituted” are as described for thoseof the “substituent in the case of ‘substituted or unsubstituted’”. Thearbitrary substituent is preferably an alkyl group having 1 to 50 carbonatoms or an aryl group having 6 to 50 ring carbon atoms, and details ofthe alkyl group and the aryl group are as described above.

The compound represented by the formula (1) is preferably any oneselected from the group of the following compounds.

As described above, the “hydrogen atom” referred in the descriptionherein encompasses a protium atom, a deuterium atom, and tritium atom.Accordingly, the inventive compound may contain a naturally-deriveddeuterium atom.

A deuterium atom may be intentionally introduced into the inventivecompound by using a deuterated compound as a art or the whole of the rawmaterial. Accordingly, in one embodiment of the present disclosure, theinventive compound contains at least one deuterium atom. That is, theinventive compound may be a compound represented by the formula (1) inwhich at least one hydrogen atom contained in the compound is adeuterium atom.

At least one hydrogen atom selected from the following hydrogen atomsmay be a deuterium atom:

a hydrogen atom that any of R¹ to R⁴ represents; a hydrogen atom thatthe substituted or unsubstituted alkyl group of any of R¹ to R⁴ has;

a hydrogen atom that any of R⁵ to R⁹ represents; a hydrogen atom thatthe substituted or unsubstituted alkyl group or the substituted orunsubstituted phenyl group of any of R⁵ to R⁹ has;

a hydrogen atom that any of R¹¹ to R¹⁵, R²¹ to R²⁶, R³¹ to R³⁵, R⁴¹ toR⁴⁸, R⁵¹ to R⁶² and R⁷¹ to R⁷⁸ represents; a hydrogen atom that thesubstituted or unsubstituted alkyl group, the substituted orunsubstituted cycloalkyl group, the substituted or unsubstituted arylgroup or the substituted or unsubstituted heterocyclic group of any ofR¹¹ to R¹⁵, R²¹ to R²⁶, R³¹ to R³⁵, R⁴¹ to R⁴⁸, R⁵¹ to R⁶² and R⁷¹ toR⁷⁸ has;

a hydrogen atom that R⁸¹ represents; a hydrogen atom that thesubstituted or unsubstituted alkyl group, the substituted orunsubstituted aryl group or the substituted or unsubstitutedheterocyclic group of R⁸¹ has;

a hydrogen atom that the phenylene group bonding to the central nitrogenatom specified on the formula (1) has (that is, a hydrogen atom that thering D in the following formula (1D) has); and

a hydrogen atom that an unsubstituted phenylene group not bonding to thecentral nitrogen atom specified on the formula (1) has (that is, ahydrogen atom that the ring E in the following formula (1D) has).

In the formula (1D), Ar¹, Ar², R¹ to R⁹, *a, *b and *1 to *3 are asdefined in the formula (1).

The deuteration rate of the inventive compound depends on thedeuteration rate of the raw material compound used. Even when a rawmaterial having a predetermined deuteration rate is used, anaturally-derived protium isotope can be contained in a certain ratio.Accordingly, an embodiment of the deuteration rate of the inventivecompound shown below includes the proportion for which a minor amount ofa naturally-derived isotope is taken into consideration, relative to theproportion determined by counting the number of the deuterium atomsmerely represented by a chemical formula.

The deuteration rate of the inventive compound is preferably 1% or more,more preferably 3% or more, even more preferably 5% or more, furthermore preferably 10% or more, further more preferably 50% or more.

The inventive compound may be a mixture of a deuterated compound and anon-deuterated compound, or a mixture of two or more compounds havingdifferent deuteration rates from each other. The deuteration rate of themixture is preferably 1% or more, more preferably 3% or more, even morepreferably 5% or more, further more preferably 10% or more, further morepreferably 50% or more, and is less than 100%.

The proportion of the number of the deuterium atoms to the number of allthe hydrogen atoms in the inventive compound is preferably 1% or more,more preferably 3% or more, even more preferably 5% or more, furthermore preferably 10% or more, and is 100% or less.

The inventive compound can be readily produced by a person skilled inthe art with reference to the following synthesis examples and the knownsynthesis methods.

Specific examples of the inventive compound will be described below, butthe inventive compound is not limited to the following examplecompounds.

Material for Organic EL Devices

The material for organic EL devices of the present invention containsthe inventive compound. The content of the inventive compound in thematerial for organic EL devices may be 1% by mass or more (including100%), and is preferably 10% by mass or more (including 100%), morepreferably 50% by mass or more (including 100%), further preferably 80%by mass or more (including 100%), still further preferably 90% by massor more (including 100%). The material for organic EL devices of thepresent invention is useful for the production of an organic EL device.

Organic EL Device

The organic EL device of the present invention includes an anode, acathode, and organic layers intervening between the anode and thecathode. The organic layers include a light emitting layer, and at leastone layer of the organic layers contains the inventive compound.

Examples of the organic layer containing the inventive compound includea hole transporting zone (such as a hole injecting layer, a holetransporting layer, an electron blocking layer, and an exciton blockinglayer) intervening between the anode and the light emitting layer, thelight emitting layer, a space layer, and an electron transporting zone(such as an electron injecting layer, an electron transporting layer,and a hole blocking layer) intervening between the cathode and the lightemitting layer, but are not limited thereto. The inventive compound ispreferably used as a material for the hole transporting zone or thelight emitting layer in a fluorescent or phosphorescent EL device, morepreferably as a material for the hole transporting zone, furtherpreferably as a material for the hole injecting layer, the holetransporting layer, the electron blocking layer, or the exciton blockinglayer, and particularly preferably as a material for the hole injectinglayer or the hole transporting layer.

The organic EL device of the present invention may be a fluorescent orphosphorescent light emission-type monochromatic light emitting deviceor a fluorescent/phosphorescent hybrid-type white light emitting device,and may be a simple type having a single light emitting unit or a tandemtype having a plurality of light emitting units. Above all, thefluorescent light emission-type device is preferred. The “light emittingunit” referred to herein refers to a minimum unit that emits lightthrough recombination of injected holes and electrons, which includesorganic layers among which at least one layer is a light emitting layer.

For example, as a representative device configuration of the simple typeorganic EL device, the following device configuration may beexemplified.

(1) Anode/Light Emitting Unit/Cathode

The light emitting unit may be a multilayer type having a plurality ofphosphorescent light emitting layers or fluorescent light emittinglayers. In this case, a space layer may intervene between the lightemitting layers for the purpose of preventing excitons generated in thephosphorescent light emitting layer from diffusing into the fluorescentlight emitting layer. Representative layer configurations of the simpletype light emitting unit are described below. Layers in parentheses areoptional.

(a) (hole injecting layer/) hole transporting layer/fluorescent lightemitting layer/electron transporting layer (/electron injecting layer)

(b) (hole injecting layer/) hole transporting layer/phosphorescent lightemitting layer/electron transporting layer (/electron injecting layer)

(c) (hole injecting layer/) hole transporting layer/first fluorescentlight emitting layer/second fluorescent light emitting layer/electrontransporting layer (/electron injecting layer)

(d) (hole injecting layer/) hole transporting layer/first phosphorescentlight emitting layer/second phosphorescent light emitting layer/electrontransporting layer (/electron injecting layer)

(e) (hole injecting layer/) hole transporting layer/phosphorescent lightemitting layer/space layer/fluorescent light emitting layer/electrontransporting layer (/electron injecting layer)

(f) (hole injecting layer/) hole transporting layer/first phosphorescentlight emitting layer/second phosphorescent light emitting layer/spacelayer/fluorescent light emitting layer/electron transporting layer(/electron injecting layer)

(g) (hole injecting layer/) hole transporting layer/first phosphorescentlight emitting layer/space layer/second phosphorescent light emittinglayer/space layer/fluorescent light emitting layer/electron transportinglayer (/electron injecting layer)

(h) (hole injecting layer/) hole transporting layer/phosphorescent lightemitting layer/space layer/first fluorescent light emitting layer/secondfluorescent light emitting layer/electron transporting layer (/electroninjecting layer)

(i) (hole injecting layer/) hole transporting layer/electron blockinglayer/fluorescent light emitting layer/electron transporting layer(/electron injecting layer)

(j) (hole injecting layer/) hole transporting layer/electron blockinglayer/phosphorescent light emitting layer/electron transporting layer(/electron injecting layer)

(k) (hole injecting layer/) hole transporting layer/exciton blockinglayer/fluorescent light emitting layer/electron transporting layer(/electron injecting layer)

(l) (hole injecting layer/) hole transporting layer/exciton blockinglayer/phosphorescent light emitting layer/electron transporting layer(/electron injecting layer)

(m) (hole injecting layer/) first hole transporting layer/second holetransporting layer/fluorescent light emitting layer/electrontransporting layer (/electron injecting layer)

(n) (hole injecting layer/) first hole transporting layer/second holetransporting layer/phosphorescent light emitting layer/electrontransporting layer (/electron injecting layer)

(o) (hole injecting layer/) first hole transporting layer/second holetransporting layer/fluorescent light emitting layer/first electrontransporting layer/second electron transporting layer (/electroninjecting layer)

(p) (hole injecting layer/) first hole transporting layer/second holetransporting layer/phosphorescent light emitting layer/first electrontransporting layer/second electron transporting layer (/electroninjecting layer)

(q) (hole injecting layer/) hole transporting layer/fluorescent lightemitting layer/hole blocking layer/electron transporting layer(/electron injecting layer)

(r) (hole injecting layer/) hole transporting layer/phosphorescent lightemitting layer/hole blocking layer/electron transporting layer(/electron injecting layer)

(s) (hole injecting layer/) hole transporting layer/fluorescent lightemitting layer/exciton blocking layer/electron transporting layer(/electron injecting layer)

(t) (hole injecting layer/) hole transporting layer/phosphorescent lightemitting layer/exciton blocking layer/electron transporting layer(/electron injecting layer)

The phosphorescent and fluorescent light emitting layers may emitemission colors different from each other, respectively. Specifically,in the light emitting unit (f), a layer configuration, such as (holeinjecting layer/) hole transporting layer/first phosphorescent lightemitting layer (red light emission)/second phosphorescent light emittinglayer (green light emission)/space layer/fluorescent light emittinglayer (blue light emission)/electron transporting layer, may beexemplified.

An electron blocking layer may be properly provided between each lightemitting layer and the hole transporting layer or the space layer. Ahole blocking layer may be properly provided between each light emittinglayer and the electron transporting layer. The employment of theelectron blocking layer or the hole blocking layer allows to improve theemission efficiency by trapping electrons or holes within the lightemitting layer and increasing the probability of charge recombination inthe light emitting layer.

As a representative device configuration of the tandem type organic ELdevice, the following device configuration may be exemplified.

(2) Anode/First Light Emitting Unit/Intermediate Layer/Second LightEmitting Unit/Cathode

For example, each of the first light emitting unit and the second lightemitting unit may be independently selected from the above-describedlight emitting units.

The intermediate layer is also generally referred to as an intermediateelectrode, an intermediate conductive layer, a charge generation layer,an electron withdrawing layer, a connecting layer, or an intermediateinsulating layer, and a known material configuration can be used, inwhich electrons are supplied to the first light emitting unit, and holesare supplied to the second light emitting unit.

FIG. 1 is a schematic illustration showing an example of theconfiguration of the organic EL device of the present invention. Theorganic EL device 1 of this example includes a substrate 2, an anode 3,a cathode 4, and a light emitting unit 10 disposed between the anode 3and the cathode 4. The light emitting unit 10 includes a light emittinglayer 5. A hole transporting zone 6 (such as a hole injecting layer anda hole transporting layer) is provided between the light emitting layer5 and the anode 3, and an electron transporting zone 7 (such as anelectron injecting layer and an electron transporting layer) is providedbetween the light emitting layer 5 and the cathode 4. In addition, anelectron blocking layer (which is not shown in the figure) may beprovided on the side of the anode 3 of the light emitting layer 5, and ahole blocking layer (which is not shown in the figure) may be providedon the side of the cathode 4 of the light emitting layer 5. According tothe configuration, electrons and holes are trapped in the light emittinglayer 5, thereby enabling one to further increase the productionefficiency of excitons in the light emitting layer 5.

FIG. 2 is a schematic illustration showing another configuration of theorganic EL device of the present invention. An organic EL device 11includes the substrate 2, the anode 3, the cathode 4, and a lightemitting unit 20 disposed between the anode 3 and the cathode 4. Thelight emitting unit 20 includes the light emitting layer 5. A holetransporting zone disposed between the anode 3 and the light emittinglayer 5 includes a hole injecting layer 6 a, a first hole transportinglayer 6 b and a second hole transporting layer 6 c. The electrontransporting zone disposed between the light emitting layer 5 and thecathode 4 includes a first electron transporting layer 7 a and a secondelectron transporting layer 7 b.

In the present invention, a host combined with a fluorescent dopant (afluorescent emitting material) is referred to as a fluorescent host, anda host combined with a phosphorescent dopant is referred to as aphosphorescent host. The fluorescent host and the phosphorescent hostare not distinguished from each other merely by the molecular structuresthereof. Specifically, the phosphorescent host means a material thatforms a phosphorescent light emitting layer containing a phosphorescentdopant, but does not mean unavailability as a material that forms afluorescent light emitting layer. The same also applies to thefluorescent host.

Substrate

The substrate is used as a support of the organic EL device. Examples ofthe substrate include a plate of glass, quartz, and plastic. Inaddition, a flexible substrate may be used. Examples of the flexiblesubstrate include a plastic substrate made of polycarbonate,polyarylate, polyether sulfone, polypropylene, polyester, polyvinylfluoride, or polyvinyl chloride. In addition, an inorganic vapordeposition film can be used.

Anode

It is preferred that a metal, an alloy, an electrically conductivecompound, or a mixture thereof which has a high work function(specifically 4.0 eV or more) is used for the anode formed on thesubstrate. Specific examples thereof include indium oxide-tin oxide(ITO: Indium Tin Oxide), indium oxide-tin oxide containing silicon orsilicon oxide, indium oxide-zinc oxide, indium oxide containing tungstenoxide and zinc oxide, and graphene. Besides, examples thereof includegold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr),molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd),titanium (Ti), or nitrides of the metals (for example, titaniumnitride).

These materials are usually deposited by a sputtering method. Forexample, through a sputtering method, it is possible to form indiumoxide-zinc oxide by using a target in which 1 to 10 wt % of zinc oxideis added to indium oxide, and to form indium oxide containing tungstenoxide and zinc oxide by using a target containing 0.5 to 5 wt % oftungsten oxide and 0.1 to 1 wt % of zinc oxide with respect to indiumoxide. Besides, the manufacturing may be performed by a vacuum vapordeposition method, a coating method, an inkjet method, a spin coatingmethod, or the like.

The hole injecting layer formed in contact with the anode is formed byusing a material that facilitates hole injection regardless of a workfunction of the anode, and thus, it is possible to use materialsgenerally used as an electrode material (for example, metals, alloys,electrically conductive compounds, or mixtures thereof, elementsbelonging to Group 1 or 2 of the periodic table of the elements). It isalso possible to use elements belonging to Group 1 or 2 of the periodictable of the elements, which are materials having low work functions,that is, alkali metals, such as lithium (Li) and cesium (Cs), alkalineearth metals, such as magnesium (Mg), calcium (Ca), and strontium (Sr),and alloys containing these (such as MgAg and AlLi), and rare earthmetals, such as europium (Eu), and ytterbium (Yb) and alloys containingthese. When the anode is formed by using the alkali metals, the alkalineearth metals, and alloys containing these, a vacuum vapor depositionmethod or a sputtering method can be used. Further, when a silver pasteor the like is used, a coating method, an inkjet method, or the like canbe used.

Hole Injecting Layer

The hole injecting layer is a layer containing a material having a highhole injection capability (a hole injecting material) and is providedbetween the anode and the light emitting layer, or between the holetransporting layer, if exists, and the anode.

As the hole injecting material except the inventive compound, molybdenumoxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide,chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silveroxide, tungsten oxide, and manganese oxide can be used.

Examples of the hole injecting layer material also include aromaticamine compounds as low-molecular weight organic compounds, such as4,4′,4″-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA),4,4′,4″-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine(abbreviation: MTDATA),4,4′-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation:DPAB),4,4′-bis(N-{4-[N′-(3-methylphenyl)-N′-phenylamino]phenyl}-N-phenylamino)biphenyl(abbreviation: DNTPD),1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene(abbreviation: DPA3B),3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole(abbreviation: PCzPCA1),3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole(abbreviation: PCzPCA2), and3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole(abbreviation: PCzPCN1).

High-molecular weight compounds (such as oligomers, dendrimers, andpolymers) may also be used. Examples thereof include high-molecularweight compounds, such as poly(N-vinylcarbazole) (abbreviation: PVK),poly(4-vinyltriphenylamine) (abbreviation: PVTPA),poly[N-(4-{N′-[4-(4-diphenylamino)phenyl]phenyl-N′-phenylamino}phenyl)methacrylamide](abbreviation:PTPDMA), and poly[N,N′-bis(4-butylphenyl)-N,N′-bis(phenyl)benzidine](abbreviation: Poly-TPD). In addition, high-molecular weight compoundsto which an acid is added, such as poly(3,4-ethylenedioxythiophene)/poly(styrene sulfonic acid) (PEDOT/PSS), and polyaniline/poly(styrenesulfonic acid) (PAni/PSS), can also be used.

Furthermore, it is also preferred to use an acceptor material, such as ahexaazatriphenylene (HAT) compound represented by formula (K).

In the aforementioned formula, R₂₁ to R₂₆ each independently represent acyano group, —CONH₂, a carboxy group, or —COOR₂₇ (R₂₇ represents analkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 3to 20 carbon atoms). In addition, adjacent two selected from R₂₁ andR₂₂, R₂₃ and R₂₄, and R₂₅ and R₂₆ may be bonded to each other to form agroup represented by —CO—O—CO—.

Examples of R₂₇ include a methyl group, an ethyl group, an n-propylgroup, an isopropyl group, an n-butyl group, an isobutyl group, at-butyl group, a cyclopentyl group, and a cyclohexyl group.

Hole Transporting Layer

The hole transporting layer is a layer containing a material having ahigh hole transporting capability (a hole transporting material) and isprovided between the anode and the light emitting layer, or between thehole injecting layer, if exists, and the light emitting layer. Theinventive compound can be used as the hole transporting layer eithersingly or as combined with the compound mentioned below.

The hole transporting layer may have a single layer structure or amultilayer structure including two or more layers. For example, the holetransporting layer may have a two-layer structure including a first holetransporting layer (anode side) and a second hole transporting layer(cathode side). In one embodiment of the present invention, the holetransporting layer having a single layer structure is preferablydisposed adjacent to the light emitting layer, and the hole transportinglayer that is closest to the cathode in the multilayer structure, suchas the second hole transporting layer in the two-layer structure, ispreferably disposed adjacent to the light emitting layer. In anotherembodiment of the present invention, and an electron blocking layerdescribed later may be disposed between the hole transporting layerhaving a single layer structure and the light emitting layer, or betweenthe hole transporting layer that is closest to the light emitting layerin the multilayer structure and the light emitting layer.

In the hole transporting layer of a two-layer structure, the inventivecompound may be in the first hole transporting layer or the second holetransporting layer, or may be in the two.

In one embodiment of the present invention, the inventive compound ispreferably contained in the first hole transporting layer alone, and inanother embodiment, the inventive compound is preferably contained inthe second hole transporting layer alone, and in still anotherembodiment, the inventive compound is preferably contained in the firsthole transporting layer and the second hole transporting layer.

In one embodiment of the present invention, the inventive compoundcontained in one or both of the first hole transporting layer and thesecond hole transporting layer is preferably a protium compound from theviewpoint of production cost.

The protium compound is the inventive compound where all hydrogen atomsare protium atoms.

Accordingly, the present invention includes an organic EL device whereone or both of the first hole transporting layer and the second holetransporting layer contain the inventive compound of substantially aprotium compound alone. The “inventive compound of substantially aprotium compound alone” means that the content ratio of a protiumcompound relative to the total amount of the inventive compound is 90mol % or more, preferably 95 mol % or more, more preferably 99 mol % ormore (each inclusive of 100%).

As the hole transporting material except the inventive compound, forexample, an aromatic amine compound, a carbazole derivative, and ananthracene derivative can be used.

Examples of the aromatic amine compound include4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB) orN,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1′-biphenyl]-4,4′-diamine(abbreviation: TPD), 4-phenyl-4′-(9-phenylfluoren-9-yl)triphenylamine(abbreviation: BAFLP),4,4′-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl(abbreviation: DFLDPBi), 4,4′,4″-tris(N,N-diphenylamino)triphenylamine(abbreviation: TDATA),4,4′,4″-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine(abbreviation: MTDATA), and4,4′-bis[N-(spiro-9,9′-bifluoren-2-yl)-N-phenylamino]biphenyl(abbreviation: BSPB). The aforementioned compounds have a hole mobilityof 10-6 cm²/Vs or more.

Examples of the carbazole derivative include4,4′-di(9-carbazolyl)biphenyl (abbreviation: CBP),9-[4-(9-carbazolyl)phenyl]-10-phenylanthracene (abbreviation: CzPA), and9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation:PCzPA).

Examples of the anthracene derivative include2-t-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA),9,10-di(2-naphthyl)anthracene (abbreviation: DNA), and9,10-diphenylanthracene (abbreviation: DPAnth).

High-molecular weight compounds, such as poly(N-vinylcarbazole)(abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation:PVTPA), can also be used.

However, compounds other than those as mentioned above can also be usedso long as they are compounds high in the hole transporting capabilityrather than in the electron transporting capability.

Dopant Material of Light Emitting Layer

The light emitting layer is a layer containing a material having a highlight emitting property (a dopant material), and various materials canbe used. For example, a fluorescent emitting material or aphosphorescent emitting material can be used as the dopant material. Thefluorescent emitting material is a compound that emits light from asinglet excited state, and the phosphorescent emitting material is acompound that emits light from a triplet excited state.

Examples of a blue-based fluorescent emitting material that can be usedfor the light emitting layer include a pyrene derivative, a styrylaminederivative, a chrysene derivative, a fluoranthene derivative, a fluorenederivative, a diamine derivative, and a triarylamine derivative.Specific examples thereof includeN,N′-bis[4-(9H-carbazole-9-yl)phenyl]-N,N′-diphenylstilbene-4,4′-diamine(abbreviation: YGA2S),4-(9H-carbazole-9-yl)-4′-(10-phenyl-9-anthryl)triphenylamine(abbreviation: YGAPA), and4-(10-phenyl-9-anthryl)-4′-(9-phenyl-9H-carbazole-3-yl)triphenylamine(abbreviation: PCBAPA).

Examples of a green-based fluorescent emitting material that can be usedfor the light emitting layer include an aromatic amine derivative.Specific examples thereof includeN-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazole-3-amine(abbreviation: 2PCAPA),N-[9,10-bis(1,1′-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazole-3-amine(abbreviation: 2PCABPhA),N-(9,10-diphenyl-2-anthryl)-N,N′,N′-triphenyl-1,4-phenylenediamine(abbreviation: 2DPAPA),N-[9,10-bis(1,1′-biphenyl-2-yl)-2-anthryl]-N,N′,N′-triphenyl-1,4-phenylenediamine(abbreviation: 2DPABPhA),N-[9,10-bis(1,1′-biphenyl-2-yl)]-N-[4-(9H-carbazole-9-yl)phenyl]-N-phenylanthracene-2-amine(abbreviation: 2YGABPhA), and N,N,9-triphenylanthracene-9-amine(abbreviation: DPhAPhA).

Examples of a red-based fluorescent emitting material that can be usedfor the light emitting layer include a tetracene derivative and adiamine derivative. Specific examples thereof includeN,N,N′,N′-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviation:p-mPhTD) and7,14-diphenyl-N,N,N′,N′-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine(abbreviation: p-mPhAFD).

Examples of a blue-based phosphorescent emitting material that can beused for the light emitting layer include a metal complex, such as aniridium complex, an osmium complex, and a platinum complex. Specificexamples thereof includebis[2-(4′,6′-difluorophenyl)pyridinato-N,C2′]iridium(III)tetrakis(1-pyrazolyl)borate(abbreviation: FIr6),bis[2-(4′,6′-difluorophenyl)pyridinato-N,C2′]iridium(III)picolinate(abbreviation: FIrpic), bis[2-(3′,5′bistrifluoromethylphenyl)pyridinato-N,C2′]iridium(III)picolinate(abbreviation: Ir(CF3ppy)2(pic)), andbis[2-(4′,6′-difluorophenyl)pyridinato-N,C2′]iridium(III)acetylacetonate(abbreviation: FIracac).

Examples of a green-based phosphorescent emitting material that can beused for the light emitting layer include an iridium complex. Examplesthereof include tris(2-phenylpyridinato-N,C2′)iridium(III)(abbreviation: Ir(ppy)3),bis(2-phenylpyridinato-N,C2′)iridium(III)acetylacetonate (abbreviation:Ir(ppy)2(acac)),bis(1,2-diphenyl-1H-benzimidazolato)iridium(III)acetylacetonate(abbreviation: Ir(pbi)2(acac)), andbis(benzo[h]quinolinato)iridium(III)acetylacetonate (abbreviation:Ir(bzq)2(acac)).

Examples of a red-based phosphorescent emitting material that can beused for the light emitting layer include a metal complex, such as aniridium complex, a platinum complex, a terbium complex, and a europiumcomplex. Specific examples thereof include organic metal complexes, suchasbis[2-(2′-benzo[4,5-a]thienyl)pyridinato-N,C3′]iridium(III)acetylacetonate(abbreviation: Ir(btp)2(acac)),bis(1-phenylisoquinolinato-N,C2′)iridium(III)acetylacetonate(abbreviation: Ir(piq)2(acac)),(acetylacetonate)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III)(abbreviation: Ir(Fdpq)2(acac)), and2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrinplatinum(II)(abbreviation: PtOEP).

Rare earth metal complexes, such as tris(acetylacetonate)(monophenanthroline)terbium(III) (abbreviation: Tb(acac)3(Phen)),tris(1,3-diphenyl-1,3-propanedionate)(monophenanthroline)europium(III)(abbreviation: Eu(DBM)3(Phen)), andtris[1-(2-thenoyl)-3,3,3-trifluoroacetonate](monophenanthroline)europium(III)(abbreviation: Eu(TTA)3(Phen)), emit light from rare earth metal ions(electron transition between different multiplicities), and thus may beused as the phosphorescent emitting material.

Host Material of Light Emitting Layer

The light emitting layer may have a configuration in which theaforementioned dopant material is dispersed in another material (a hostmaterial). The host material is preferably a material that has a higherlowest unoccupied orbital level (LUMO level) and a lower highestoccupied orbital level (HOMO level) than the dopant material.

Examples of the host material include:

(1) a metal complex, such as an aluminum complex, a beryllium complex,and a zinc complex,

(2) a heterocyclic compound, such as an oxadiazole derivative, abenzimidazole derivative, and a phenanthroline derivative,

(3) a fused aromatic compound, such as a carbazole derivative, ananthracene derivative, a phenanthrene derivative, a pyrene derivative,and a chrysene derivative, or

(4) an aromatic amine compound, such as a triarylamine derivative and afused polycycic aromatic amine derivative.

For example,

metal complexes, such as tris(8-quinolinolato)aluminum(III)(abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum(III)(abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium(II)(abbreviation: BeBq2),bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III)(abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Zng),bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), andbis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ);

heterocyclic compounds, such as2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation:PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene(abbreviation: OXD-7),3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole(abbreviation: TAZ),2,2′,2″-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole)(abbreviation: TPBI), bathophenanthroline (abbreviation: BPhen), andbathocuproine (abbreviation: BCP);

fused aromatic compounds, such as9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: CzPA),3,6-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole(abbreviation: DPCzPA), 9,10-bis(3,5-diphenylphenyl)anthracene(abbreviation: DPPA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA),2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA),9,9′-bianthryl(abbreviation: BANT),9,9′-(stilbene-3,3′-diyl)diphenanthrene (abbreviation: DPNS),9,9′-(stilbene-4,4′-diyl)diphenanthrene (abbreviation: DPNS2),3,3′,3″-(benzene-1,3,5-triyl)tripyrene (abbreviation: TPB3),9,10-diphenylanthracene (abbreviation: DPAnth), and6,12-dimethoxy-5,11-diphenylchrysene; and

aromatic amine compounds, such asN,N-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole-3-amine(abbreviation: CzA1PA), 4-(10-phenyl-9-anthryl)triphenylamine(abbreviation: DPhPA),N,9-diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole-3-amine(abbreviation: PCAPA),N,9-diphenyl-N-{4-[4-(10-phenyl-9-anthryl)phenyl]phenyl}-9H-carbazole-3-amine(abbreviation: PCAPBA),N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazole-3-amine(abbreviation: 2PCAPA), 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl(abbreviation: NPB or α-NPD),N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1′-biphenyl]-4,4′-diamine(abbreviation: TPD),4,4′-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl(abbreviation: DFLDPBi), and4,4′-bis[N-(spiro-9,9′-bifluoren-2-yl)-N-phenylamino]biphenyl(abbreviation: BSPB) can be used. A plurality of host materials may beused.

In particular, in the case of a blue fluorescent device, it is preferredto use the following anthracene compounds as the host material.

Electron Transporting Layer

The electron transporting layer is a layer containing a material havinga high electron transporting capability (an electron transportingmaterial) and is provided between the light emitting layer and thecathode, or between the electron injecting layer, if exists, and thelight emitting layer.

The electron transporting layer may have a single layer structure or amultilayer structure including two or more layers. For example, theelectron transporting layer may have a two-layer structure including afirst electron transporting layer (anode side) and a second electrontransporting layer (cathode side). In one embodiment of the presentinvention, the electron transporting layer having a single layerstructure is preferably disposed adjacent to the light emitting layer,and the electron transporting layer that is closest to the anode in themultilayer structure, such as the first electron transporting layer inthe two-layer structure, is preferably disposed adjacent to the lightemitting layer. In another embodiment of the present invention, and ahole blocking layer described later may be disposed between the electrontransporting layer having a single layer structure and the lightemitting layer, or between the electron transporting layer that isclosest to the light emitting layer in the multilayer structure and thelight emitting layer.

As the electron transporting layer, for example,

(1) a metal complex, such as an aluminum complex, a beryllium complex,and a zinc complex;

(2) a heteroaromatic compound, such as an imidazole derivative, abenzimidazole derivative, an azine derivative, a carbazole derivative,and a phenanthroline derivative; and

(3) a high-molecular weight compound can be used.

Examples of the metal complex include tris(8-quinolinolato)aluminum(III)(abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum(abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium(abbreviation: BeBq₂),bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III)(abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq),bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), andbis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ).

Examples of the heteroaromatic compound include2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation:PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene(abbreviation: OXD-7),3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole(abbreviation: TAZ),3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole(abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen),bathocuproine (abbreviation: BCP), and4,4′-bis(5-methylbenzxazol-2-yl)stilbene (abbreviation: BzOs).

Examples of the high-molecular weight compound includepoly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)](abbreviation: PF-Py), andpoly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2′-bipyridine-6,6′-diyl)](abbreviation: PF-BPy).

The materials are materials having an electron mobility of 10-6 cm²/Vsor more. Materials other than those as mentioned above may also be usedin the electron transporting layer so long as they are materials high inthe electron transporting capability rather than in the holetransporting capability.

Electron Injecting Layer

The electron injecting layer is a layer containing a material having ahigh electron injection capability. As the electron injecting layer,alkali metals, such as lithium (Li) and cesium (Cs), alkaline earthmetals, such as magnesium (Mg), calcium (Ca), and strontium (Sr), rareearth metals, such as europium (Eu) and ytterbium (Yb), and compoundscontaining these metals can be used. Examples of the compounds includean alkali metal oxide, an alkali metal halide, an alkalimetal-containing organic complex, an alkaline earth metal oxide, analkaline earth metal halide, an alkaline earth metal-containing organiccomplex, a rare earth metal oxide, a rare earth metal halide, and a rareearth metal-containing organic complex. These compounds may be used as amixture of a plurality thereof.

In addition, a material having an electron transporting capability, inwhich an alkali metal, an alkaline earth metal, or a compound thereof iscontained, specifically Alq in which magnesium (Mg) is contained may beused. In this case, electron injection from the cathode can be moreefficiently performed.

Otherwise, in the electron injecting layer, a composite materialobtained by mixing an organic compound with an electron donor may beused. Such a composite material is excellent in the electron injectioncapability and the electron transporting capability because the organiccompound receives electrons from the electron donor. In this case, theorganic compound is preferably a material excellent in transportingreceived electrons, and specifically, examples thereof include amaterial constituting the aforementioned electron transporting layer(such as a metal complex and a heteroaromatic compound). As the electrondonor, a material having an electron donation property for the organiccompound may be used. Specifically, alkali metals, alkaline earthmetals, and rare earth metals are preferred, and examples thereofinclude lithium, cesium, magnesium, calcium, erbium, and ytterbium. Inaddition, an alkali metal oxide or an alkaline earth metal oxide ispreferred, and examples thereof include lithium oxide, calcium oxide,and barium oxide. In addition, a Lewis base, such as magnesium oxide,can also be used. In addition, an organic compound, such astetrathiafulvalene (abbreviation: TTF), can also be used.

Cathode

It is preferred that a metal, an alloy, an electrically conductivecompound, or a mixture thereof which has a low work function(specifically 3.8 eV or less) is used for the cathode. Specific examplesof such a cathode material include elements belonging to group 1 or 2 ofthe periodic table of the elements, that is, alkali metals, such aslithium (Li) and cesium (Cs), alkaline earth metals, such as magnesium(Mg), calcium (Ca), and strontium (Sr), and alloys containing these(such as MgAg, and AlLi), and rare earth metals, such as europium (Eu),and ytterbium (Yb) and alloys containing these.

When the cathode is formed by using the alkali metals, the alkalineearth metals, and the alloys containing these, a vacuum vapor depositionmethod or a sputtering method can be adopted. In addition, when a silverpaste or the like is used, a coating method, an inkjet method, or thelike can be adopted.

By providing the electron injecting layer, the cathode can be formedusing various conductive materials, such as Al, Ag, ITO, graphene, andindium oxide-tin oxide containing silicon or silicon oxide regardless ofthe magnitude of a work function. Such a conductive material can bedeposited by using a sputtering method, an inkjet method, a spin coatingmethod, or the like.

Insulating Layer

The organic EL device applies an electric field to an ultrathin film,and thus, pixel defects are likely to occur due to leaks orshort-circuiting. In order to prevent this, an insulating layer formedof an insulating thin film layer may be inserted between a pair ofelectrodes.

Examples of the material used for the insulating layer include aluminumoxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide,magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride,aluminum nitride, titanium oxide, silicon oxide, germanium oxide,silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, andvanadium oxide. A mixture or a laminate of these may also be used.

Space Layer

The space layer is, for example, a layer provided between a fluorescentlight emitting layer and a phosphorescent light emitting layer for thepurpose of preventing excitons generated in the phosphorescent lightemitting layer from diffusing into the fluorescent light emitting layer,or adjusting a carrier balance, in the case where the fluorescent lightemitting layers and the phosphorescent light emitting layers arestacked. The space layer can also be provided among the plurality ofphosphorescent light emitting layers.

Since the space layer is provided between the light emitting layers, amaterial having both an electron transporting capability and a holetransporting capability is preferred. Also, one having a triplet energyof 2.6 eV or more is preferred in order to prevent triplet energydiffusion in the adjacent phosphorescent light emitting layer. Examplesof the material used for the space layer include the same as those usedfor the hole transporting layer as described above.

Blocking Layer

The blocking layer such as the electron blocking layer, the holeblocking layer, or the exciton blocking layer may be provided adjacentto the light emitting layer. The electron blocking layer is a layer thatprevents electrons from leaking from the light emitting layer to thehole transporting layer, and the hole blocking layer is a layer thatprevents holes from leaking from the light emitting layer to theelectron transporting layer. The exciton blocking layer has a functionof preventing excitons generated in the light emitting layer fromdiffusing into the surrounding layers, and trapping the excitons withinthe light emitting layer.

Each layer of the organic EL device may be formed by a conventionallyknown vapor deposition method, a coating method, or the like. Forexample, formation can be performed by a known method using a vapordeposition method such as a vacuum vapor deposition method, or amolecular beam vapor deposition method (MBE method), or a coating methodusing a solution of a compound for forming a layer, such as a dippingmethod, a spin-coating method, a casting method, a bar-coating method,and a roll-coating method.

The film thickness of each layer is not particularly limited, but istypically 5 nm to 10 μm, and more preferably 10 nm to 0.2 μm because ingeneral, when the film thickness is too small, defects such as pinholesare likely to occur, and conversely, when the film thickness is toolarge, a high driving voltage is required and the efficiency decreases.

The organic EL device can be used for electronic devices, such asdisplay components of an organic EL panel module, display devices of atelevision, a mobile phone and a personal computer, and light emittingdevices of lightings and vehicular lamps.

EXAMPLES

The present disclosure is hereunder described in more detail byreference to Examples, but it should be construed that the presentdisclosure is not limited to the following Examples.

Inventive Compounds Used for Production of Organic EL Devices ofExamples 1 to 22

Comparative Compounds Used for Production of Organic EL Devices ofComparative Examples 1 to 4

Other Compounds Used for Production of Organic EL Devices

Production of Organic EL Device Example 1

A glass substrate of 25 mm×75 mm×1.1 mm provided with an ITO transparentelectrode (anode) (manufactured by GEOMATEC Co., Ltd.) wasultrasonically cleaned in isopropyl alcohol for 5 minutes and thensubjected to UV ozone cleaning for 30 minutes. The film thickness of theITO was 130 nm.

The cleaned glass substrate provided with the transparent electrode wasmounted on a substrate holder of a vacuum vapor deposition apparatus,and firstly, Compound HT1 and Compound HI1 were vapor co-deposited onthe surface having the transparent electrode formed thereon, so as tocover the transparent electrode, resulting in a hole injecting layerwith a film thickness of 10 nm. The mass ratio of Compound HT1 toCompound HI1 (HT1/HI1) was 97/3.

Subsequently, on this hole injecting layer, Compound HT1 was vapordeposited to form a first hole transporting layer with a film thicknessof 80 nm.

Subsequently, on this first hole transporting layer, Compound Inv-2 wasvapor deposited to form a second hole transporting layer with a filmthickness of 10 nm.

Subsequently, on this second hole transporting layer, Compound BH (hostmaterial) and Compound BD (dopant material) were vapor co-deposited toform a light emitting layer with a film thickness of 25 nm. The massratio of Compound BH to Compound BD (BH/BD) was 96/4.

Subsequently, on this light emitting layer, Compound ET1 was vapordeposited to form a first electron transporting layer with a filmthickness of 10 nm.

Subsequently, on this first electron transporting layer, Compound ET2and Liq were vapor co-deposited to form a second electron transportinglayer with a film thickness of 15 nm. The mass ratio of Compound ET2 toLiq (Compound ET2/Liq) was 50/50.

Subsequently, on this second electron transporting layer, LiF was vapordeposited to form an electron injecting electrode with a film thicknessof 1 nm.

Then, on this electron injecting electrode, metal Al was vapor depositedto form a metal cathode with a film thickness of 80 nm.

The layer configuration of the organic EL device of Example 1 thusobtained was as follows.

ITO (130)/(HT1/HI1=97/3) (10)/HT1 (80)/Compound Inv-2 (10)/(BH/BD=96/4)(25)/ET1 (10)/(ET2/Liq=50/50) (15)/LiF (1)/Al (80)

In the layer configuration, the numeral in parentheses indicates thefilm thickness (nm), and the ratio is a mass ratio.

Comparative Example 1

An organic EL device was produced in the same manner as in Example 1except that Comparative Compound Ref-1 was used in place of CompoundInv-2.

Examples 2 to 22, Comparative Examples 2 to 4

Organic EL Devices of Examples 2 to 22 and Comparative Examples 2 to 4were produced in the same manner as in Example 1, except that CompoundsInv-1, 3 to 22 and Comparative Compounds Ref-2 to 4, respectively, wereused in place of Compound Inv-2 and that HT2 was used in place ofCompound HT1 in the hole injecting layer and Compound HT1 in the firsthole transporting layer.

Measurement of Device Lifetime (LT90)

The resulting organic EL device was emitted by driving at roomtemperature with DC direct current at a current density of 50 mA/cm²,and the period of time until the luminance was reduced to 90% of theinitial luminance was measured, and was defined as 90% lifetime (LT90).The results are shown in Tables 1 and 2.

Measurement of External Quantum Efficiency (EQE)

The resulting organic EL device was driven at room temperature with DCdirect current at a current density of 10 mA/cm². Using a luminancemeter (spectral radiance meter CS-1000 by Konica Minolta, Inc.), theluminance of the device was measured, and from the found data, theexternal quantum efficiency (%) was derived. The results are shown inTable 1.

TABLE 1 Material of Second Hole Transporting LT90 (hrs) @ EQE (%) @Layer 50 mA/cm² 10 mA/cm² Example 1 Compound Inv-2 94 9.7 ComparativeComparative 85 9.3 Example 1 Compound Ref-1

TABLE 2 Material of Second Hole LT90 (hrs) @ Transporting Layer 50mA/cm² Example 2 Compound Inv-1 127 Example 3 Compound Inv-3 139 Example4 Compound Inv-4 135 Example 5 Compound Inv-5 147 Example 6 CompoundInv-6 115 Example 7 Compound Inv-7 193 Example 8 Compound Inv-8 58Example 9 Compound Inv-9 73 Example 10 Compound Inv-10 89 Example 11Compound Inv-11 103 Example 12 Compound Inv-12 82 Example 13 CompoundInv-13 108 Example 14 Compound Inv-14 132 Example 15 Compound Inv-15 140Example 16 Compound Inv-16 139 Example 17 Compound Inv-17 111 Example 18Compound Inv-18 140 Example 19 Compound Inv-19 145 Example 20 CompoundInv-20 149 Example 21 Compound Inv-21 149 Example 22 Compound Inv-22 140Reference Example 2 Reference Compound Ref-2 49 Reference Example 3Reference Compound Ref-3 19 Reference Example 4 Reference Compound Ref-452

From the results in Tables 1 and 2, it is known that the organic ELdevices containing Inventive Compound (Compound Inv-1 to 22) have alonger lifetime than the organic EL devices containing ReferenceCompound (Ref-1 to 4), Also from the results in Table 1, it is knownthat the organic EL device containing Inventive Compound (CompoundInv-2) has a higher light emission efficiency than the organic EL devicecontaining Comparative Compound (Ref-1).

Inventive Compounds Synthesized in Synthesis Examples

Synthesis Example 1: Synthesis of Compound Inv-1

Synthesis of Intermediate A

In an argon atmosphere, 85.0 g of 3,4-dibromoaniline, 99.0 g ofphenylboronic acid, 7.83 g of tetrakis(triphenylphosphine)palladium(0),813 ml of an aqueous solution of 2 M sodium carbonate, and 800 ml of1,2-dimethoxyethane were mixed and stirred at 80° C. for 3 hours.Subsequently, this was extracted with ethyl acetate. The organic layerwas dried with anhydrous magnesium sulfate, and then concentrated, andthe residue was purified through silica gel column chromatography togive 78.5 g of [1,1′:2′,1″-terphenyl]-4′-amine (Intermediate A). Theyield was 94%.

Synthesis of Intermediate B

In an argon atmosphere, 25.0 g of (1,1′:2′,1″-terphenyl)-4′-amine and360 mL of acetonitrile were put in a flask and completely dissolved. Tothis, 58.2 g of p-toluenesulfonic acid was added, and then set at 0° C.To the mixture, 180 mL of an aqueous solution of 42.3 g of potassiumiodide and 14.1 g of sodium nitrite was dropwise added taking 30minutes. With cooling with ice, this was stirred for 30 minutes, then600 mL of water was added, and while restoring to room temperature, thiswas stirred for further 2 hours. Subsequently, the resulting solid wastaken out through filtration, and this was dissolved in 500 mL oftoluene, and further an aqueous solution of sodium sulfate was added forextraction. The organic layer was dried with anhydrous magnesiumsulfate, then concentrated, and washed with hexane to give 29.0 g of4′-iodo-1,1′:2′,1″-terphenyl (Intermediate B). The yield was 80%.

Synthesis of Intermediate C

In an argon atmosphere, 22.5 g of Intermediate B, 9.88 g of4-chlorophenylboronic acid, 1.34 g ofdichlorobis[di-tert-butyl(4-dimethylaminophenyl)phosphine]palladium(II),60 mL of an aqueous solution of 2 M sodium carbonate, and 240 mL of1,2-dimethoxyethane were mixed, and stirred at 80° C. for 1.5 hours.Subsequently, water was added, and the precipitated solid was taken outthrough filtration. The solid was recrystallized with a mixed solvent oftoluene and hexane to give 18.3 g of4′-(4-chlorophenyl)-1,1′:2′1″-terphenyl (Intermediate C). The yield was85%.

Synthesis of Compound Inv-1

In an argon atmosphere, 3.18 g ofN-([1,1′-biphenyl]-4-yl)naphthalene-1-amine, 3.50 g of Intermediate C,0.188 g of tris(dibenzylideneacetone)dipalladium(0), 0.238 g oftri-t-butylphosphonium tetrafluoroborate, 1.48 g of sodium-t-butoxideand 50 mL of toluene were mixed, and stirred at 110° C. for 5 hours. Thereaction mixture was cooled at room temperature, and then concentratedunder reduced pressure. The resulting residue was purified throughsilica gel column chromatography and recrystallization with a mixedsolvent of toluene and hexane to give 3.36 g of a white solid. The yieldwas 55%.

The resulting product was Compound Inv-1 as a result of massspectrometry (m/e=600 relative to molecular weight 599.78).

Synthesis Example 2: Synthesis of Compound Inv-2

In an argon atmosphere, 3.75 g ofN-(4-(dibenzo[b,d]furan-4-yl)phenyl)naphthalene-1-amine, 3.25 g ofIntermediate C, 0.175 g of tris(dibenzylideneacetone)dipalladium(0),0.221 g of tri-t-butylphosphonium tetrafluoroborate, 1.38 g ofsodium-t-butoxide, and 53 mL of toluene were mixed, and stirred at 110°C. for 4 hours. The reaction mixture was cooled at room temperature, andthen concentrated under reduced pressure. The resulting residue waspurified through silica gel column chromatography and recrystallizationwith a mixed solvent of toluene and hexane to give 4.23 g of a whitesolid. The yield was 64%.

The resulting product was Compound Inv-2 as a result of massspectrometry (m/e=690 relative to molecular weight 689.86).

Synthesis Example 3: Synthesis of Compound Inv-3

Synthesis of Intermediate D

In an argon atmosphere, 3.75 g of 1-naphthalene-2,3,4,5,6,7,8-d₇-amine,3.25 g of bromobenzene d₅, 0.175 g oftris(dibenzylideneacetone)dipalladium(0), 0.221 g oftri-t-butylphosphonium tetrafluoroborate, 5.24 g of sodium-t-butoxide,and 53 mL of toluene were mixed, and stirred at 110° C. for 4 hours. Thereaction mixture was cooled at room temperature, and then concentratedunder reduced pressure. The resulting residue was purified throughsilica gel column chromatography and recrystallization with a mixedsolvent of toluene and hexane to give 8.75 g of a white solid,Intermediate D. The yield was 77%.

Synthesis of Intermediate E

In an argon atmosphere, 4.99 g of Intermediate D, 6.45 g ofN-bromosuccinimide, and 180 mL of dichloromethane (dewatered) weremixed, and stirred at room temperature for 4 hours. Subsequently, 100 mLof water was added, and this was stirred at room temperature for 1 hour.Subsequently, this was extracted with dichloromethane. The organic layerwas dried with anhydrous magnesium sulfate, then concentrated, and theresidue was purified through silica gel column chromatography andrecrystallization with a mixed solvent of toluene and hexane to give6.78 g of a yellow solid, Intermediate E. The yield was 80%.

Synthesis of Intermediate F

In an argon atmosphere, 4.42 g of Intermediate E, 5.39 g ofbis(pinacolato)diboron, 0.064 g of palladium(II) acetate, 0.270 g of2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (XPhos), 7.55 g ofpotassium acetate, and 80 ml of 1.4-dioxane (dewatered) were mixed, andstirred at 100° C. for 4 hours. Subsequently, 50 mL of water was added,and this was stirred at room temperature for 1 hour. Subsequently, thiswas extracted with dichloromethane. The organic layer was dried withanhydrous magnesium sulfate, and then concentrated under reducedpressure. The resulting residue was purified through silica gel columnchromatography to give 6.44 g of a white solid, Intermediate F. Theyield was 81%.

Synthesis of Intermediate G

In an argon atmosphere, 3.99 g of Intermediate F, 0.74 mL ofbromobenzene, 0.164 g of tetrakis(triphenylphosphine)palladium(0), 40 mLof an aqueous solution of 2 M sodium carbonate, and 100 mL of1,2-dimethoxyethane were mixed, and stirred at 80° C. for 3 hours.Subsequently, this was extracted with toluene. The organic layer wasdried with anhydrous magnesium sulfate, then concentrated, and theresidue was purified through silica gel column chromatography to give2.26 g of Intermediate G. The yield was 62%.

Synthesis of Compound Inv-3

In an argon atmosphere, 2.53 g of Intermediate G, 1.76 g of4′-iodo-1,1′:2′,1″-terphenyl, 0.114 g oftetrakis(triphenylphosphine)palladium(0), 14 mL of an aqueous solutionof 2 M sodium carbonate, and 40 mL of 1,2-dimethoxyethane were mixed,and stirred at 80° C. for 3 hours. Subsequently, this was extracted withtoluene. The organic layer was dried with anhydrous magnesium sulfate,then concentrated, and the residue was purified through silica gelcolumn chromatography to give 2.09 g of a white solid. The yield was69%.

As a result of mass spectrometry (m/e=615 relative to molecular weight614.87), the resulting product was Compound Inv-3.

Synthesis Example 4: Synthesis of Compound Inv-4

In an argon atmosphere, 3.33 g of di-([1,1′-biphenyl]-4-yl)amine, 3.54 gof Intermediate C, 0.196 g of tris(dibenzylideneacetone)dipalladium(0),0.240 g of tri-t-butylphosphonium tetrafluoroborate, 2.99 g ofsodium-t-butoxide and 58 mL of toluene were mixed, and stirred at 110°C. for 4 hours. The reaction mixture was cooled at room temperature andthen concentrated under reduced pressure. The resulting residue waspurified through silica gel column chromatography and recrystallizationwith a mixed solvent of toluene and hexane to give 4.67 g of a whitesolid. The yield was 72%.

The resulting product was Compound Inv-4 as a result of massspectrometry (m/e=626 relative to molecular weight 625.82).

Synthesis Example 5: Synthesis of Compound Inv-5

In an argon atmosphere, 3.21 g ofN-(4-(naphthalene-1-yl)phenyl)naphthalene-1-amine, 3.25 g ofIntermediate C, 0.170 g of tris(dibenzylideneacetone)dipalladium(0),0.216 g of tri-t-butylphosphonium tetrafluoroborate, 2.68 g ofsodium-t-butoxide and 53 mL of toluene were mixed, and stirred at 110°C. for 4 hours. The reaction mixture was cooled at room temperature andthen concentrated under reduced pressure. The resulting residue waspurified through silica gel column chromatography and recrystallizationwith a mixed solvent of toluene and hexane to give 6.04 g of a whitesolid. The yield was 68%.

The resulting product was Compound Inv-5 as a result of massspectrometry (m/e=650 relative to molecular weight 649.84).

Synthesis Example 6: Synthesis of Compound Inv-6

In an argon atmosphere, 3.01 g ofN-(4-(dibenzo[b,d]furan-4-yl)phenyl)-[1,1′-biphenyl]-4-amine, 2.97 g ofIntermediate C, 0.160 g of tris(dibenzylideneacetone)dipalladium(0),0.202 g of tri-t-butylphosphonium tetrafluoroborate, 2.51 g ofsodium-t-butoxide and 48 mL of toluene were mixed, and stirred at 110°C. for 4 hours. The reaction mixture was cooled at room temperature andthen concentrated under reduced pressure. The resulting residue waspurified through silica gel column chromatography and recrystallizationwith a mixed solvent of toluene and hexane to give 4.42 g of a whitesolid. The yield was 78%.

The resulting product was Compound Inv-6 as a result of massspectrometry (m/e=650 relative to molecular weight 649.84).

Synthesis Example 7: Synthesis of Compound Inv-7

In an argon atmosphere, 3.61 g of4-(dibenzo[b,d]furan-4-yl)-N-phenylaniline, 3.67 g of Intermediate C,0.197 g of tris(dibenzylideneacetone)dipalladium(0), 0.250 g oftri-t-butylphosphonium tetrafluoroborate, 3.10 g of sodium-t-butoxideand 60 mL of toluene were mixed, and stirred at 110° C. for 4 hours. Thereaction mixture was cooled at room temperature and then concentratedunder reduced pressure. The resulting residue was purified throughsilica gel column chromatography and recrystallization with a mixedsolvent of toluene and hexane to give 5.58 g of a white solid. The yieldwas 81%.

The resulting product was Compound Inv-7 as a result of massspectrometry (m/e=690 relative to molecular weight 689.86).

Synthesis Example 8: Synthesis of Compound Inv-8

In an argon atmosphere, 2.85 g ofN-([1,1′-biphenyl]-4-yl)dibenzo[b,d]furan-1-amine, 2.89 g ofIntermediate C, 0.155 g of tris(dibenzylideneacetone)dipalladium(0),0.201 g of tri-t-butylphosphonium tetrafluoroborate, 2.45 g ofsodium-t-butoxide and 47 mL of toluene were mixed, and stirred at 110°C. for 4 hours. The reaction mixture was cooled at room temperature andthen concentrated under reduced pressure. The resulting residue waspurified through silica gel column chromatography and recrystallizationwith a mixed solvent of toluene and hexane to give 3.69 g of a whitesolid. The yield was 68%.

The resulting product was Compound Inv-8 as a result of massspectrometry (m/e=639 relative to molecular weight 639.26).

Synthesis Example 9: Synthesis of Compound Inv-9

In an argon atmosphere, 5.86 g ofN-([1,1′-biphenyl]-4-yl)-9,9-biphenyl-9H-fluorene-4-amine, 4.10 g ofIntermediate C, 0.220 g of tris(dibenzylideneacetone)dipalladium(0),0.285 g of tri-t-butylphosphonium tetrafluoroborate, 3.48 g ofsodium-t-butoxide and 67 mL of toluene were mixed, and stirred at 110°C. for 4 hours. The reaction mixture was cooled at room temperature andthen concentrated under reduced pressure. The resulting residue waspurified through silica gel column chromatography and recrystallizationwith a mixed solvent of toluene and hexane to give 5.23 g of a whitesolid. The yield was 55%.

The resulting product was Compound Inv-9 as a result of massspectrometry (m/e=789 relative to molecular weight 789.34).

Synthesis Example 10: Synthesis of Compound Inv-10

In an argon atmosphere, 2.73 g of4-(naphthalen-1-yl)-N-[4-(naphthalen-1-yl)phenyl]aniline, 2.20 g ofIntermediate C, 0.118 g of tris(dibenzylideneacetone)dipalladium(0),0.153 g of tri-t-butylphosphonium tetrafluoroborate, 1.87 g ofsodium-t-butoxide and 36 mL of toluene were mixed, and stirred at 110°C. for 4 hours. The reaction mixture was cooled at room temperature andthen concentrated under reduced pressure. The resulting residue waspurified through silica gel column chromatography and recrystallizationwith a mixed solvent of toluene and hexane to give 3.84 g of a whitesolid. The yield was 82%.

The resulting product was Compound Inv-10 as a result of massspectrometry (m/e=725 relative to molecular weight 725.31).

Synthesis Example 11: Synthesis of Compound Inv-11

In an argon atmosphere, 3.51 g ofN-[4-(naphthalen-1-yl)phenyl][1,1′-biphenyl]-4-amine, 3.21 g ofIntermediate C, 0.172 g of tris(dibenzylideneacetone)dipalladium(0),0.223 g of tri-t-butylphosphonium tetrafluoroborate, 2.72 g ofsodium-t-butoxide and 52 mL of toluene were mixed, and stirred at 110°C. for 4 hours. The reaction mixture was cooled at room temperature andthen concentrated under reduced pressure. The resulting residue waspurified through silica gel column chromatography and recrystallizationwith a mixed solvent of toluene and hexane to give 4.65 g of a whitesolid. The yield was 73%.

The resulting product was Compound Inv-11 as a result of massspectrometry (m/e=675 relative to molecular weight 675.29).

Synthesis Example 12: Synthesis of Compound Inv-12

In an argon atmosphere, 5.33 g ofN-[4-(dibenzo[b,d]furan-1-yl)phenyl][1,1′-biphenyl]-4-amine, 4.40 g ofIntermediate C, 0.236 g of tris(dibenzylideneacetone)dipalladium(0),0.306 g of tri-t-butylphosphonium tetrafluoroborate, 3.73 g ofsodium-t-butoxide and 72 mL of toluene were mixed, and stirred at 110°C. for 4 hours. The reaction mixture was cooled at room temperature andthen concentrated under reduced pressure. The resulting residue waspurified through silica gel column chromatography and recrystallizationwith a mixed solvent of toluene and hexane to give 6.93 g of a whitesolid. The yield was 75%.

The resulting product was Compound Inv-12 as a result of massspectrometry (m/e=715 relative to molecular weight 715.29).

Synthesis Example 13: Synthesis of Compound Inv-13

In an argon atmosphere, 4.14 g of4-(naphthalen-2-yl)-N-[4-(naphthalen-2-yl)phenyl]aniline, 3.34 g ofIntermediate C, 0.179 g of tris(dibenzylideneacetone)dipalladium(0),0.232 g of tri-t-butylphosphonium tetrafluoroborate, 2.83 g ofsodium-t-butoxide and 54 mL of toluene were mixed, and stirred at 110°C. for 4 hours. The reaction mixture was cooled at room temperature andthen concentrated under reduced pressure. The resulting residue waspurified through silica gel column chromatography and recrystallizationwith a mixed solvent of toluene and hexane to give 4.91 g of a whitesolid. The yield was 69%.

The resulting product was Compound Inv-13 as a result of massspectrometry (m/e=725 relative to molecular weight 725.31).

Synthesis Example 14: Synthesis of Compound Inv-14

In an argon atmosphere, 3.63 g ofN-[4-(phenanthren-9-yl)phenyl]naphthalene-1-amine, 3.12 g ofIntermediate C, 0.168 g of tris(dibenzylideneacetone)dipalladium(0),0.217 g of tri-t-butylphosphonium tetrafluoroborate, 2.65 g ofsodium-t-butoxide and 51 mL of toluene were mixed, and stirred at 110°C. for 4 hours. The reaction mixture was cooled at room temperature andthen concentrated under reduced pressure. The resulting residue waspurified through silica gel column chromatography and recrystallizationwith a mixed solvent of toluene and hexane to give 5.32 g of a whitesolid. The yield was 82%.

The resulting product was Compound Inv-14 as a result of massspectrometry (m/e=699 relative to molecular weight 699.29).

Synthesis Example 15: Synthesis of Compound Inv-15

In an argon atmosphere, 4.28 g ofN-([1,1′-biphenyl]-4-yl)-3′-(9H-carbazol-9-yl)[1,1′-biphenyl]-4-amine,2.99 g of Intermediate C, 0.161 g oftris(dibenzylideneacetone)dipalladium(0), 0.208 g oftri-t-butylphosphonium tetrafluoroborate, 2.54 g of sodium-t-butoxideand 48 mL of toluene were mixed, and stirred at 110° C. for 4 hours. Thereaction mixture was cooled at room temperature and then concentratedunder reduced pressure. The resulting residue was purified throughsilica gel column chromatography and recrystallization with a mixedsolvent of toluene and hexane to give 5.90 g of a white solid. The yieldwas 85%.

The resulting product was Compound Inv-15 as a result of massspectrometry (m/e=790 relative to molecular weight 790.33).

Synthesis Example 16: Synthesis of Compound Inv-16

In an argon atmosphere, 3.96 g ofN-([1,1′-biphenyl]-4-yl)-2′-(9H-carbazol-9-yl)[1,1′-biphenyl]-4-amine,2.77 g of Intermediate C, 0.148 g oftris(dibenzylideneacetone)dipalladium(0), 0.192 g oftri-t-butylphosphonium tetrafluoroborate, 2.35 g of sodium-t-butoxideand 45 mL of toluene were mixed, and stirred at 110° C. for 4 hours. Thereaction mixture was cooled at room temperature and then concentratedunder reduced pressure. The resulting residue was purified throughsilica gel column chromatography and recrystallization with a mixedsolvent of toluene and hexane to give 4.89 g of a white solid. The yieldwas 76%.

The resulting product was Compound Inv-16 as a result of massspectrometry (m/e=790 relative to molecular weight 790.33).

Synthesis Example 17: Synthesis of Compound Inv-17

In an argon atmosphere, 5.39 g ofN-[4-(dibenzo[b,d]furan-4-yl)phenyl]dibenzo[b,d]furan-1-amine, 4.31 g ofIntermediate C, 0.232 g of tris(dibenzylideneacetone)dipalladium(0),0.299 g of tri-t-butylphosphonium tetrafluoroborate, 3.66 g ofsodium-t-butoxide and 70 mL of toluene were mixed, and stirred at 110°C. for 4 hours. The reaction mixture was cooled at room temperature andthen concentrated under reduced pressure. The resulting residue waspurified through silica gel column chromatography and recrystallizationwith a mixed solvent of toluene and hexane to give 5.45 g of a whitesolid. The yield was 59%.

The resulting product was Compound Inv-17 as a result of massspectrometry (m/e=729 relative to molecular weight 729.27).

Synthesis Example 18: Synthesis of Compound Inv-18

Synthesis of Intermediate H

In an argon atmosphere, 5.68 g (25.9 mmol) of3-(naphthalen-1-yl)aniline, 6.58 g (25.9 mmol) of 1-iodo-naphthalene,474 mg (0.51 mmol) of tris(dibenzylideneacetone)dipalladium(0), 645 mg(1.03 mmol) of BINAP, 2.74 g (28.5 mmol) of sodium-t-butoxide and 130 mLof toluene were mixed and stirred under heat at 110° C. for 7 hours.After left cooled, this was filtered and the resulting residue waspurified through column chromatography to give 7.49 g of Intermediate H.The yield was 84%.

Synthesis of Compound Inv-18

In an argon atmosphere, 3.2 g of Intermediate H, 3.27 g of IntermediateC, 0.176 g of tris(dibenzylideneacetone)dipalladium(0), 0.222 g oftri-t-butylphosphonium tetrafluoroborate, 2.70 g of sodium-t-butoxideand 54 mL of toluene were mixed, and stirred at 110° C. for 4 hours. Thereaction mixture was cooled at room temperature and then concentratedunder reduced pressure. The resulting residue was purified throughsilica gel column chromatography and recrystallization with a mixedsolvent of toluene and hexane to give 6.05 g of a white solid. The yieldwas 68%.

The resulting product was Compound Inv-18 as a result of massspectrometry (m/e=650 relative to molecular weight 649.84).

Synthesis Example 19: Synthesis of Compound Inv-19

Synthesis of Intermediate I

In an argon atmosphere, 2.19 g (22.33 mmol) of aniline-2,3,4,5,6-d5,3.29 g (20.3 mmol) of bromobenzene-d5, 372 mg (0.41 mmol) oftris(dibenzylideneacetone)dipalladium(0), 506 mg (0.812 mmol) of BINAP,2.15 g (22.33 mmol) of sodium-t-butoxide and 200 mL of toluene weremixed and stirred under heat at 100° C. for 3 hours. After left cooled,this was filtered and the resulting residue was purified through columnchromatography to give 3.59 g of Intermediate I. The yield was 99%.

Synthesis of Intermediates J and K

In an argon atmosphere, 2.9 g (16.18 mmol) of Intermediate I and 55 mLof DMF were mixed, and at 0° C., 5.76 g (32.4 mmol) ofN-bromosuccinimide was added thereto. Water and ethyl acetate were addedfor extraction, and the resulting organic layer was distilled underreduced pressure to give Intermediate J. Intermediate J was subjected tothe next reaction without purification.

In an argon atmosphere, 6.41 g (19.12 mmol) of Intermediate J, 5.83 g(47.8 mmol) of phenylboronic acid, 406 mg (0.574 mmol) ofbis(di-t-butyl(4-dimethylaminophenyl)phosphine) dichloropalladium(II)and 1,4-dioxane (100 mL) were mixed, and an aqueous solution ofpotassium phosphate was added thereto. This was stirred under heat at110° C. for 5 hours, then left cooled, and the mixture was filtered andpurified by column chromatography and recrystallization to give 3.9 g ofIntermediate K. The yield of Intermediate K produced via Intermediate Jwas 62% (2 steps).

Synthesis of Compound Inv-19

In an argon atmosphere, 2.64 g of Intermediate J, 2.86 g of IntermediateC, 0.147 g of tris(dibenzylideneacetone)dipalladium(0), 0.186 g oftri-t-butylphosphonium tetrafluoroborate, 1.08 g of sodium-t-butoxideand 80 mL of toluene were mixed, and stirred at 110° C. for 7 hours. Thereaction mixture was cooled at room temperature and then concentratedunder reduced pressure. The resulting residue was purified throughsilica gel column chromatography and recrystallization with a mixedsolvent of toluene and hexane to give 3.29 g of a white solid. The yieldwas 65%.

The resulting product was Compound Inv-19 as a result of massspectrometry (m/e=633 relative to molecular weight 633.33).

Synthesis Example 20: Synthesis of Compound Inv-20

Synthesis of Intermediate L

In an argon atmosphere, 8.61 g (30 mmol) of1-bromo-4-iodobenzene-2,3,5,6-d4, 8.63 g (31.5 mmol) of[1,1′:2′,1″-terphenyl]-4′-ylboronic acid, 1.39 g (1.2 mmol) oftetrakis(triphenylphosphine)palladium(0), 30 mL of an aqueous solutionof 2 M tripotassium phosphate, and 150 mL of dioxane were mixed andstirred under heat at 80° C. for 7 hours. Water was added and theprecipitated solid was extracted with dichloromethane and washed. Thesolvent was evaporated away, and the resulting residue was purifiedthrough column chromatography to give Intermediate L (7.3 g). The yieldwas 63%.

Synthesis of Compound Inv-20

In an argon atmosphere, 2.64 g of Intermediate K, 3.27 g of IntermediateL, 0.147 g of tris(dibenzylideneacetone)dipalladium(0), 0.186 g oftri-t-butylphosphonium tetrafluoroborate, 1.08 g of sodium-t-butoxideand 80 mL of toluene were mixed, and stirred at 110° C. for 7 hours. Thereaction mixture was cooled at room temperature and then concentratedunder reduced pressure. The resulting residue was purified throughsilica gel column chromatography and recrystallization with a mixedsolvent of toluene and hexane to give 4.11 g of a white solid. The yieldwas 80%.

The resulting product was Compound Inv-20 as a result of massspectrometry (m/e=637 relative to molecular weight 637.35).

Synthesis Example 21: Synthesis of Compound Inv-21

Synthesis of Intermediate M

In an argon atmosphere, 6.0 g (15.41 mmol) of Intermediate L, 23.12 mLof a toluene solution of 1 M LiHMDS, 282 mg (0.31 mmol) oftris(dibenzylideneacetone)dipalladium(0), 179 mg (0.62 mmol) oftri-t-butylphosphonium tetrafluoroborate and 77 mL of toluene were mixedand stirred under heat at 110° C. for 7 hours. Hydrochloric acid wasadded and this was extracted with toluene, and the resulting residue waspurified through column chromatography to give 3.45 g of Intermediate M.The yield was 69%.

Synthesis of Intermediate N

In an argon atmosphere, 3.45 g (10.6 mmol) of Intermediate M, 2.69 g(10.6 mmol) of 1-iodonaphthalene, 194 mg (0.212 mmol) oftris(dibenzylideneacetone)dipalladium(0), 264 mg (0.424 mmol) of BINAP,1.12 g (11.6 mmol) of sodium-t-butoxide and 53 mL of toluene were mixedand stirred under heat at 100° C. for 8 hours. The residue was purifiedthrough column chromatography to give 3.8 g of Intermediate N. The yieldwas 80%.

Synthesis of Intermediate O

In an argon atmosphere, 2.87 g (10 mmol) of1-bromo-4-iodobenzene-2,3,5,6-d4, 1.81 g (10.5 mmol) of1-naphthaleneboronic acid, 462 mg (0.4 mmol) oftetrakis(triphenylphosphine)palladium(0), 10 mL of an aqueous solutionof 2 M tripotassium phosphate, and 50 mL of dioxane were mixed andstirred under heat at 80° C. for 7 hours. The reaction liquid waspurified through column chromatography to give Intermediate O (2.87 g).The yield was 99%.

Synthesis of Compound Inv-21

In an argon atmosphere, 1.82 g of Intermediate N, 1.39 g of IntermediateO, 0.074 g of tris(dibenzylideneacetone)dipalladium(0), 0.094 g oftri-t-butylphosphonium tetrafluoroborate, 0.542 g of sodium-t-butoxideand 40 mL of toluene were mixed, and stirred at 110° C. for 7 hours. Thereaction mixture was cooled at room temperature and then concentratedunder reduced pressure. The resulting residue was purified throughsilica gel column chromatography and recrystallization with a mixedsolvent of toluene and hexane to give 1.70 g of a white solid. The yieldwas 64%.

The resulting product was Compound Inv-21 as a result of massspectrometry (m/e=657 relative to molecular weight 657.33).

Synthesis Example 22: Synthesis of Compound Inv-22

Synthesis of Intermediate P

According to the same operation as in synthesis of Intermediate O butchanging 1-naphthaleneboronic acid to phenylboronic acid, Intermediate Pwas produced. The yield was 97%.

Synthesis of Compound Inv-22

In an argon atmosphere, 2.03 g of Intermediate N, 1.28 g of IntermediateP, 0.082 g of tris(dibenzylideneacetone)dipalladium(0), 0.104 g oftri-t-butylphosphonium tetrafluoroborate, 0.61 g of sodium-t-butoxideand 45 mL of toluene were mixed and stirred at 110° C. for 7 hours. Thereaction mixture was cooled at room temperature and then concentratedunder reduced pressure. The resulting residue was purified throughsilica gel column chromatography and recrystallization with a mixedsolvent of toluene and hexane to give 2.00 g of a white solid. The yieldwas 73%.

The resulting product was Compound Inv-22 as a result of massspectrometry (m/e=607 relative to molecular weight 607.31).

REFERENCE SIGNS LIST

-   -   1, 11: Organic EL device    -   2: Substrate    -   3: Anode    -   4: Cathode    -   5: Light emitting layer    -   6: Hole transporting zone (hole transporting layer)    -   6 a: Hole injecting layer    -   6 b: First hole transporting layer    -   6 b: Second hole transporting layer    -   7: Electron transporting zone (electron transporting layer)    -   7 a: First electron transporting layer    -   7 b: Second electron transporting layer    -   10, 20: Light emitting unit

1. A compound represented by the following formula (1):

wherein Ar¹ is a group represented by the formula (12) to (14), and Ar² is a group represented by any of the formulae (10) to (14):

wherein, R¹¹ to R¹⁵, R²¹ to R²⁶, R⁴¹ to R⁴⁸, R⁵¹ to R⁶² and R⁷¹ to R⁷⁸ each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R³¹ to R³⁵ each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms, a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, X represents an oxygen atom, a sulfur atom, or NR⁸¹, R⁸¹ represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, provided that, one selected from R¹¹ to R¹⁵ is a single bond bonding to *c, one selected from R²¹ to R²⁶ is a single bond bonding to *d, the other one selected from R²¹ to R²⁶ is a single bond bonding to *e, one selected from R⁴⁵ to R⁴⁸ is a single bond bonding to *f, one selected from R⁵⁹ to R⁶² is a single bond bonding to *g, one selected from R⁷⁵ to R⁷⁸ and R⁸¹ is a single bond bonding to *i, *h bonds to one selected from the carbon atoms *4 to *8, ** represents a bonding position to the central nitrogen atom, m is 0 or 1, n is 0 or 1, in the formulae (10) to (12) and the formula (14), when m is 0 and n is 0, *e bonds to the central nitrogen atom, when m is 0 and n is 1, *c bonds to the central nitrogen atom, and when m is 1 and n is 0, *e bonds to one selected from R¹¹ to R¹⁵, in the formula (13), when m is 0 and n is 1, *c bonds to the central nitrogen atom, when m is 1 and n is 0, *e bonds to one selected from R¹¹ to R¹⁵, a case where m is 0 and n is 0 is excluded, in the formula (14), when m is 0 and n is 1, and when m is 1 and n is 0, one selected from R⁷⁵ to R⁷⁸ is a single bond bonding to *i, adjacent two selected from R¹¹ to R¹⁵ that are not a single bond, adjacent two selected from R²¹ to R²⁶ and adjacent two selected from R³¹ to R³⁵ that are not a single bond, adjacent two selected from R⁴¹ to R⁴⁸ that are not a single bond, adjacent two selected from R⁵¹ to R⁶² that are not a single bond, and adjacent two selected from R⁷¹ to R⁷⁸ that are not a single bond do not bond to each other and therefore do not form a cyclic structure, the benzene ring A and the benzene ring B, the benzene ring A and the benzene ring C, the benzene ring B and the benzene ring C, the benzene ring A and the naphthalene ring, and the benzene ring B and the naphthalene ring do not crosslink, *a bonds to one selected from the carbon atoms *1 to *3, R¹ to R⁴ each independently represent a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, provided that, one selected from R¹ to R⁴ is a single bond bonding to *b, adjacent two selected from R¹ to R⁴ that are not a single bond bonding to *b do not bond to each other and therefore do not form a cyclic structure, R⁵ to R⁹ each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted phenyl group, provided that, adjacent two selected from R⁵ to R⁹ each independently may bond to each other to form a substituted or unsubstituted cyclic structure, or may not bond to each other and therefore may not form a cyclic structure.
 2. The compound according to claim 1, wherein Ar² is a group represented by any of the formula (20) or (21):

wherein R¹¹ to R¹⁵, R²¹, R²², R²⁴, R²⁵, R³¹ to R³⁵, R⁴¹ to R⁴⁸, **, m, n, the benzene ring A, the benzene ring B and the benzene ring C are as defined in the formula (1).
 3. The compound according to claim 1, wherein R⁴⁵ or R⁴⁶ is a single bond bonding to *f, and *h bonds to the carbon atom *8.
 4. The compound according to claim 1, wherein in the formulae (10) to (12) and the formula (14), m is 0 and n is
 0. 5. The compound according to claim 1, wherein m is 1 and n is
 1. 6. The compound according to claim 1, wherein m is 0 and n is
 1. 7. The compound according to claim 1, wherein Ar¹ is a group represented by the formula (11).
 8. The compound according to claim 1, wherein in the formula (10), m is 0 and n is 0, and R³¹ to R³⁵ are hydrogen atoms.
 9. The compound according to claim 1, wherein in the formula (10), m is 0 and n is 1, and R³¹ to R³⁵ are hydrogen atoms.
 10. The compound according to claim 1, wherein in the formula (10), m is 0 and n is 1, and R²¹ to R²⁶ that are not a single bond each are a hydrogen atom or a phenyl group, and R³¹ to R³⁵ are hydrogen atoms.
 11. The compound according to claim 1, wherein in the formula (10), m is 1 and n is 0, and R³¹ to R³⁵ are hydrogen atoms.
 12. The compound according to claim 1, wherein in the formula (10), m is 1 and n is 0, and R¹¹ to R¹⁵ that are not a single bond each are a hydrogen atom or a phenyl group, and R³¹ to R³⁵ are hydrogen atoms.
 13. The compound according to claim 1, wherein in the formula (11), m is 0 and n is
 0. 14. The compound according to claim 1, wherein in the formula (11), m is 0 and n is
 1. 15. The compound according to claim 1, wherein in the formula (11), m is 1 and n is
 0. 16. The compound according to claim 1, wherein Ar² is a substituted or unsubstituted group selected from the following formulae:


17. The compound according to claim 1, wherein R⁴⁵ is a single bond bonding to *f.
 18. The compound according to claim 1, wherein *a bonds to the carbon atom *3.
 19. The compound according to claim 1, wherein R² or R³ is a single bond bonding to *b.
 20. The compound according to claim 1, wherein R¹ to R⁴ that are not a single bond bonding to *b are all hydrogen atoms.
 21. The compound according to claim 1, wherein R⁵ to R⁹ are all hydrogen atoms.
 22. The compound according to claim 1, which is any one selected from the group of the following compounds:


23. The compound according to claim 1, wherein the compound contains at least one deuterium atom.
 24. A material for an organic electroluminescent device containing the compound of claim
 1. 25. An organic electroluminescent device comprising an anode, a cathode, and organic layers intervening between the anode and the cathode, the organic layers including a light emitting layer, at least one layer of the organic layers containing the compound of claim
 1. 26. The organic electroluminescent device according to claim 25, wherein the organic layer includes a hole transporting zone between the anode and the light emitting layer, and the hole transporting zone contains the compound.
 27. The organic electroluminescent device according to claim 26, wherein the hole transporting zone includes a first hole transporting layer positioned near the anode and a second hole transporting layer positioned near the cathode, and the first hole transporting layer, the second hole transporting layer or both the first and second hole transporting layers contain the compound.
 28. The organic electroluminescent device according to claim 27, wherein the second hole transporting layer contains the compound.
 29. The organic electroluminescent device according to claim 27, wherein the second hole transporting layer is adjacent to the light emitting layer.
 30. The organic electroluminescent device according to claim 25, wherein the light emitting layer contains a fluorescent dopant. 